Benzylhydroxylamines and intermediates used to prepare them

ABSTRACT

Benzylhydroxylamines I ##STR1## (X=--N(R 7 )--O--; Y=O, S; R 1  =halogen, CN, NO 2 , CF 3  ; R 2  =H, halogen; R 3  =H, NH 2 , CH 3  ; 
     R 4  =H, halogen, C 1  -C 6  -alkyl, C 1  -C 6  -haloalkyl, C 1  -C 6  -alkylthio, C 1  -C 6  -alkylsulfinyl or C 1  -C 6  -alkylsulfonyl; 
     R 5  =H, halogen, C 1  -C 6  -alkyl; 
     R 6  =H, C 1  -C 6  -alkyl, C 1  -C 6  -haloalkyl, C 3  -C 6  -cycloalkyl, C 2  -C 6  -alkenyl; 
     R 7  =H, C 1  -C 6  -alkyl, C 3  -C 8  -cycloalkyl, C 1  -C 6  -haloalkyl, C 3  -C 6  -alkenyl, C 3  -C 6  -alkynyl, C 1  -C 6  -alkylcarbonyl, C 3  -C 6  -alkenylcarbonyl, C 3  -C 6  -alkynylcarbonyl, C 1  -C 6  -alkoxycarbonyl, C 2  -C 8  -alkenyloxycarbonyl, C 2  -C 6  -alkynyloxycarbonyl, C 1  -C 6  -alkylthiocarbonyl, C 1  -C 6  -alkylsulfonyl, C 1  -C 6  -alkylcarbamoyl, it being possible for the 14 last-mentioned radicals to have attached to them 1-3 substituents: 
     NO 2 , CN, halogen, C 3  -C 8  -cycloalkyl, OH, C 1  -C 6  -alkoxy, C 3  -C 8  -cycloalkoxy, C 3  -C 6  -alkenyloxy, C 3  -C 6  -alkynyloxy, C 1  -C 6  -alkoxy-C 1  -C 6  -alkoxy, C 1  -C 6  -alkylthio, C 1  -C 6  -alkylcarbonyl, C 1  -C 6  -alkylcarbonyloxy, C 1  -C 6  -alkylsulfinyl, C 1  -C 6  -alkylsulfonyl, C 1  -C 6  -alkylideneaminoxy, C 1  -C 6  -alkylcarbamoyl, 
     unsubstituted or substituted phenyl, phenoxy or phenylsulfonyl, 
     a 3- to 7-membered heterocyclyl or heterocyclyloxy group having 1-3 hetero atoms, it being possible for this group to be saturated, unsaturated or aromatic and to have attached to it 1-3 substituents, 
     --CO--Z 1  R 9 , --OCO--Z 1  R 9 , --N(R 9 )R 10  or 
     R 7  =unsubstituted or substituted cycloalkylcarbonyl, phenylcarbonyl, phenylsulfonyl, phenylcarbamoyl; 
     R 8  =H, C 1  -C 6  -alkyl, C 3  -C 8  -cycloalkyl, C 1  -C 6  -haloalkyl, C 3  -C 6  -alkenyl or C 3  -C 6  -alkynyl, it being possible for each of the 5 last-mentioned radicals to have attached to it 1-3 substituents: 
     NO 2 , CN, halogen, C 3  -C 8  -cycloalkyl, OH, C 1  -C 6  -alkoxy, C 3  -C 8  -cycloalkoxy, C 3  -C 6  -alkenyloxy, C 3  -C 6  -alkynyloxy, C 1  -C 6  -alkoxy-C 1  -C 6  -alkoxy, C 1  -C 6  -alkylthio, C 1  -C 6  -alkylsulfinyl, C 1  -C 6  -alkylsulfonyl, C 1  -C 6  -alkylideneaminoxy, 
     unsubstituted or substituted phenyl- [sic], phenoxy-[sic] or phenylsulfonyl, 
     a 3- to 7-membered heterocyclyl or heterocyclyloxy group having 1-3 hetero atoms, it being possible for this group to be saturated, unsaturated or aromatic and to have attached to it 1-3 substituents, 
     --CO--Z 2  R 11 , --OCO--Z 2  R 11 , --N(R 11 )R 12  ; 
     Z 1  a chemical bond, oxygen, sulfur or --N(R 10 )--; 
     Z 2  =a chemical bond, oxygen, sulfur or --N(R 12 )--; 
     R 9 , R 11  =H, C 1  -C 6  -alkyl, C 1  -C 6  -haloalkyl, C 3  -C 8  -cycloalkyl, C 3  -C 6  -alkenyl, C 3  -C 6  -alkynyl, C 1  -C 6  -alkoxy-C 1  -C 6  -alkyl, (C 1  -C 6  -alkoxy)carbonyl-C 1  -C 6  -alkyl, unsubstituted or substituted phenyl or phenyl-C 1  -C 6  -alkyl, 
     or 
     Z 1  and R 9  and/or Z 2  and R 11  together=a 3- to 7-membered heterocycle having 1-3 hetero atoms and bonded via nitrogen, it being possible for this heterocycle to be saturated, unsaturated or aromatic and, if desired, to have attached to it one to three substituents, 
     R 10 , R 12  =H, OH, C 1  -C 6  -alkyl, C 3  -C 8  -cycloalkyl, C 1  -C 6  -alkoxy) 
     and the salts of I where R 3 , R 7  and/or R 8  =hydrogen 
     are used as herbicides and for the desiccation/defoliation of plants.

The present invention relates to novel benzylhydroxylamines of thegeneral formula I ##STR2## in which the variables have the followingmeanings: X is --N(R⁷)--O-- which can be bonded to R⁸ via oxygen ornitrogen;

Y is oxygen or sulfur;

R¹ is halogen, cyano, nitro or trifluoromethyl;

R² is hydrogen or halogen;

R³ is hydrogen, amino or methyl;

R⁴ is hydrogen, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆-alkylthio, C₁ -C₆ -alkylsulfinyl or C₁ -C₆ -alkylsulfonyl;

R⁵ is hydrogen, halogen or C₁ -C₆ -alkyl;

R⁶ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -cycloalkyl orC₂ -C₆ -alkenyl;

R⁷ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₈ -cycloalkyl, C₁ -C₆ -haloalkyl, C₃-C₆ -alkenyl, C₃ -C₆ -alkynyl, (C₁ -C₆ -alkyl)carbonyl, (C₃ -C₆-alkenyl)carbonyl, (C₃ -C₆ -alkynyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl,(C₂ -C₆ -alkenyloxy)carbonyl, (C₂ -C₆ -alkynyloxy)carbonyl, (C₁ -C₆-alkylthio)carbonyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylcarbamoyl, itoptionally being possible for each of the last-mentioned 14 radicals tohave attached to it one to three substituents in each case selected fromthe group consisting of

nitro, cyano, halogen, C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃-C₈ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆-alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, (C₁ -C₆ -alkyl)carbonyl, (C₁-C₆ -alkyl) carbonyloxy, C₁ -C₆ -alkylsulfinyl, C₁ -C₆ -alkylsulfonyl,C₁ -C₆ -alkylideneaminoxy, C₁ -C₆ -alkylcarbamoyl,

the phenyl, phenoxy or phenylsulfonyl group, it being possible for thephenyl rings to be unsubstituted or to have attached to them one tothree substituents, in each case selected from the group consisting ofhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy and C₁ -C₆-haloalkyl,

a 3- to 7-membered heterocyclyl or heterocyclyloxy group having one tothree hetero atoms, selected from the group consisting of two oxygenatoms, two sulfur atoms and 3 nitrogen atoms, it being possible for theheterocycle to be saturated, partially or fully unsaturated or aromatic,and, if desired, to have attached to it one to three substituents, ineach case selected from the group consisting of halogen, nitro, cyano,C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyl and (C₁ -C₆-alkyl)carbonyl,

a group --CO--Z¹ R⁹, --OCO--Z¹ R⁹ or --N(R⁹)R¹⁰,

or

R⁷ is C₃ -C₈ -cycloalkylcarbonyl, phenylcarbonyl, phenylsulfonyl orphenylcarbamoyl, it being possible for these 4 radicals to beunsubstituted or to have attached to them one to three substituents, ineach case selected from the group consisting of halogen, nitro, cyano,C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy and C₁ -C₆ -haloalkyl;

R⁸ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₈ -cycloalkyl, C₁ -C₆ -haloalkyl, C₃-C₆ -alkenyl or C₃ -C₆ -alkynyl, it optionally being possible for eachof the last-mentioned 5 radicals to have attached to it one to threesubstituents, in each case selected from the group consisting of

nitro, cyano, halogen, C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃-C₈ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆-alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy,

the phenyl, phenoxy or phenylsulfonyl group, it being possible for thephenyl rings to be unsubstituted or to have attached to them one tothree substituents, in each case selected from the group consisting ofnitro, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy and C₁ -C₆-haloalkyl,

a 3- to 7-membered heterocyclyl or heterocyclyloxy group having one tothree hetero atoms, selected from the group consisting of two oxygenatoms, two sulfur atoms and 3 nitrogen atoms, it being possible for theheterocycle to be saturated, partially or fully unsaturated or aromatic,and, if desired, to have attached to it one to three substituents, ineach case selected from the group consisting of halogen, nitro, cyano,C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyl and (C₁ -C₆-alkyl)carbonyl,

a group --CO--Z² R¹¹, --OCO--Z² R¹¹ or --N(R¹¹)R¹² ;

Z¹ is a chemical bond, oxygen, sulfur or --N(R¹⁰)--;

Z² is a chemical bond, oxygen, sulfur or --N(R¹²)--;

R⁹, R¹¹ independently of one another are hydrogen, C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₃ -C₈ -cycloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆-alkoxy-C₁ -C₆ -alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl, phenyl orphenyl-C₁ -C₆ -alkyl, it being possible for the phenyl group and thephenyl ring of the phenylalkyl group to be unsubstituted or to haveattached to them one to three radicals, in each case selected from thegroup consisting of nitro, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₁ -C₆ -alkoxy or (C₁ -C₆ -alkyl)carbonyl,

or

Z¹ and R⁹ and/or Z² and R¹¹ in each case together are a 3- to 7-memberedheterocycle bonded via nitrogen and having one to three hetero atomsselected from the group consisting of two oxygen atoms, two sulfur atomsand 3 nitrogen atoms, it being possible for the heterocycle to besaturated, partially or fully unsaturated or aromatic and, if desired,to have attached to it one to three substituents in each case selectedfrom the group consisting of nitro, cyano, halogen, C₁ -C₆ -alkyl, C₁-C₆ -haloalkyl and C₁ -C₆ -alkoxy;

R¹⁰, R¹² independently of one another are hydrogen, hydroxyl, C₁ -C₆-alkyl, C₃ -C₈ -cycloalkyl or C₁ -C₆ -alkoxy,

and the agriculturally useful salts of those compounds I where R³, R⁷and/or R⁸ are hydrogen.

Furthermore, the invention relates to

the use of the compounds I as herbicides or for the desiccation and/ordefoliation of plants,

herbicidal compositions and compositions for the desiccation and/ordefoliation of plants which comprise the compounds I as activeingredients,

methods of controlling undesirable vegetation and for the desiccationand/or defoliation of plants using the compounds I,

processes for the preparation of herbicidal compositions andcompositions for the desiccation and/or defoliation of plants using thecompounds I, and

novel intermediates of the formulae IV, V, XIII, XVI, XVII, XIX andXXIII, from which the compounds I can be obtained.

WO 93/06090 and EP-A 408 382 have already described certain3-phenyluracils as herbicides and for the desiccation/defoliation ofplants which--with a suitable choice of substituents--differ from thepresent compounds I especially by the fact that the phenyl ring hasattached to it an iminomethyl group instead of the substituent--CH(R⁶)--X--R⁸.

In accordance with WO 95/06641, other compounds which are also suitableas herbicides and for the desiccation/defoliation of plants are, interalia, those of the formula II ##STR3## where R^(a) is hydrogen, fluorineor chlorine and

R^(b) is, inter alia, a hydroxyiminomethyl or oxyiminomethyl group.

Finally, DE-A 42 37 920 discloses that certain 3-aryluracils, inter aliathe compounds of the formula III ##STR4## where R^(c) is hydrogen, C₁-C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ /C₄ -alkenyl or C₃ /C₄ -alkynyl;

R^(d) and R^(e) are hydrogen, C₁ -C₈ -alkyl, C₃ -C₇ -cycloalkyl or C₃-C₇ -cycloalkyl-C₁ -C₄ -alkyl;

R^(f) is hydrogen, C₁ -C⁵ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₃ -C₈-cycloalkyl, C₃ -C₈ -cycloalkyl-C₁ -C₄ -alkyl, C₁ -C₅ -haloalkyl, C₂ -C₅-alkenyl, C₂ -C₅ -alkynyl, unsubstituted or substituted aryl or benzyl,or is a keto, ester or thioester group, and

R⁵ ' is hydrogen, halogen or C₁ -C₄ -alkyl

are suitable for controlling weeds.

However, the herbicidal properties of the known compounds are not alwaysentirely satisfactory. Accordingly, it was an object of the presentinvention to provide novel, in particular herbicidally active, compoundswith which undesirable plants can be subjected to better targetedcontrol than was possible to date.

Another object was to provide novel compounds with a desiccant/defoliantaction.

Accordingly, we have found that this object is achieved by thebenzylhydroxylamines of the formula I and their herbicidal action.

Furthermore, there have been found herbicidal compositions whichcomprise the compounds I and which have a very good herbicidal action.Moreover, there have been found processes for the preparation of thesecompositions and methods of controlling undesirable vegetation using thecompounds I.

Furthermore, it has been found that the compounds I are also suitablefor the defoliation and desiccation of parts of plants, suitable plantsbeing crop plants such as cotton, potatoes, oilseed rape, sunflowers,soya beans or field beans, in particular cotton. In this respect, therehave been found compositions for the desiccation and/or defoliation ofplants, processes for the preparation of these compositions, and methodsfor the desiccation and/or defoliation of plants using the compounds I.

Depending on their substitution pattern, the compounds of the formula Ican contain one or more chiral centers, in which case they are presentas enantiomer or diastereomer mixtures. The present invention relates tothe pure enantiomers or diastereomers and also to mixtures of these.

If R³, R⁷ and/or R⁸ are hydrogen, the benzylhydroxylamines I can bepresent in the form of their agriculturally useful salts, the nature ofthe salt generally not being critical. In general, suitable salts aresalts of those bases which do not adversely affect the herbicidal actionin comparison with the free compound I.

Particularly suitable basic salts are the salts of the alkali metals,preferably sodium and potassium salts, of the alkaline earth metals,preferably calcium and magnesium salts, those of the transition metals,preferably zinc and iron salts, and ammonium salts where the ammoniumion may, if desired, have attached to it one to four C₁ -C₄ -alkyl orhydroxy-C₁ -C₄ -alkyl substituents and/or a phenyl or benzylsubstituent, preferably diisopropylammonium, tetramethylammonium,tetrabutylammonium, trimethylbenzylammonium- andtrimethyl(2-hydroxyethyl)ammonium salts, furthermore phosphonium salts,sulfonium salts, such as, preferably, tri(C₁ -C₄ -alkyl)sulfonium salts,and sulfoxonium salts such as, preferably, tri(C₁ -C₄ -alkyl)sulfoxoniumsalts.

The organic moieties mentioned for the substituents R⁴ to R¹² or asradicals on phenyl rings or heterocycles are collective terms forindividual enumerations of the individual members of the groups. Allcarbon chains, i.e. all alkyl, haloalkyl, alkoxy, alkylthio,alkylsulfenyl [sic], alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl,alkenyl, alkenyloxy, alkenylcarbonyl, alkynyl, alkynyloxy,alkynylcarbonyl and alkylideneaminooxy moieties can be straight-chain orbranched. Unless otherwise specified, halogenated substituentspreferably have attached to them one to five identical or differenthalogen atoms. The meaning halogen is in each case fluorine, chlorine,bromine or iodine.

Other examples of meanings are

C₁ -C₄ -alkyl and the alkyl moieties of (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆-alkyl)carbonyloxy, C₁ -C₆ -alkylcarbamoyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyland (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl: methyl, ethyl, n-propyl,1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl,3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropl[sic], 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or1-ethyl-2-methylpropyl;

C₁ -C₆ -haloalkyl: a C₁ -C₆ -alkyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, e.g. chloromethyl, dichloromethyl, trichloromethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl,2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,2,2,2-trichloroethyl, petafluoroethyl [sic], 2-fluoropropyl,3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl,3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl,3,3,3-trifluoropropyl, 3,3,3-trichloropropyl,2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl,4-bromobutyl, nonafluorobutyl, 5-fluoropentyl, 5-chloropentyl,5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl,6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;

phenyl-C₁ -C₆ -alkyl: e.g. benzyl, 1-phenylethyl, 2-phenylethyl,1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl,1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl,1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 3-phenylbut-2-yl,4-phenylbut-2-yl, 1-(phenylmethyl)eth-1-yl,1-(phenylmethyl)-1-(methyl)-eth-1-yl or 1-(phenylmethyl)prop-1-yl,preferably benzyl, 2-phenylethyl or 2-phenyl-hex-6-yl;

C₃ -C₆ -alkenyl and the alkenyl moieties of C₃ -C₆ -alkenyloxy and (C₃-C₆ -alkenyl)carbonyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl,n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methylprop-1-en-1-yl,2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl or2-methylprop-2-en-1-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl,n-penten-4-yl, 1-methyl-but-1-en-1-yl, 2-methylbut-1-en-1-yl,3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl,3-methyl-but-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl,1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl,1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, n-hex-1-en-1-yl,n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl,1-methylpent-1-en-1-yl, 2-mmethylpent-1-en-1-yl [sic],3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl,2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl,1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl,4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl,3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,1,1-dimethylbut-2-en-1-yl, 1,1-dimethylput-3-en-1-yl [sic],1,2-dimethylbut-1-en-1-yl, 1,2-dimetylput-2-en-1-yl [sic],1,2-dimethylbut-3-en-1-yl, 1,3-dimetylput-1-en-1-yl [sic],1,3-dimethylbut-2-en-1-yl, 1,3-dimetylput-3-en-1-yl [sic],2,2-dimethylbut-3-en-1-yl, 2,3-dimetylput-1-en-1-yl [sic],2,3-dimethylbut-2-en-1-yl, 2,3-dimetylput-3-en-1-yl [sic],3,3-dimethylbut-1-en-1-yl, 3,3-dimetylput-2-en-1-yl [sic],1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl,2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl,1-ethyl-2-methylprop-1-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl;

C₃ -C₆ -alkynyl and the alkynyl moieties of C₃ -C₆ -alkynyloxy and (C₃-C₆ -alkynyl)carbonyl: prop-1-yn-1-yl, prop-2-yn-1-yl, but-1-yn-1-yl,but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-1-yl,n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl,n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl,3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl,n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl,n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl,n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl,3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl,4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl;

C₂ -C₆ -alkenyl and the akenyl [sic] moiety of (C₂ -C₆-alkenyloxy)carbonyl: vinyl or one of the radicals mentioned for C₃ -C₆-alkenyl;

the alkynyl moiety of (C₂ -C₆ -alkynyloxy)carbonyl: ethynyl or one ofthe radicals mentioned for C₃ -C₆ -akynyl [sic];

C₁ -C₆ -alkoxy and the alkoxy moieties of C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl,(C₁ -₆ -alkoxy)carbonyl and (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl:methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy,2-methylpropoxy or 1,1-dimethylethoxy, n-pentoxy, 1-methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy,1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy;

C₁ -C₆ -alkylthio and the alkylthio moiety of (C₁ -₆-alkylthio)carbonyl: methylthio, ethylthio, n-propylthio,1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio,1,1-dimethylethylthio, n-pentylthio, 1-methylbutylthio,2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio,1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio,1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio,3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio,1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio,2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio,2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;

C₁ -C₆ -alkylsulfinyl: methylsulfinyl, ethylsulfinyl, n-propylsulfinyl,1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl,2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, n-pentylsulfinyl,1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl,2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl,1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, n-hexylsulfinyl,1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl,4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl,1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl,2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl,3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,1,1,2-trimethylproplsulfinyl [sic], 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl;

C₁ -C₆ -alkylsulfonyl: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl,1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl,2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, n-pentylsulfonyl,1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl,2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl,1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, n-hexylsulfonyl,1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl;

C₁ -C₆ -alkylideneaminoxy: acetylideneaminoxy, 1-propylideneaminoxy,2-propylideneaminoxy, 1-butylideneaminoxy, 2-butylideneaminoxy or2-hexylideneaminoxy;

C₃ -C₆ -cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or hexyl;

C₃ -C₈ -cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cycloheptyl or cyclooctyl;

C₃ -C₈ -cycloalkoxy: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,cyclohexyloxy, cycloheptyloxy or cyclooctyloxy.

Examples of 3- to 7-membered heterocycles are oxiranyl, aziridiny [sic],oxetanyl, tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl,isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl,thiazolidinyl, imidazolidinyl, dioxolanyl, such as 1,3-dioxolan-2-yl and1,3-dioxolan-4-yl, dioxanyl, such as 1,3-dioxan-2-yl and1,3-dioxan-4-yl, dithianyl, such as 1,3-dithian-2-yl, furthermore1,2,4-oxadiazolidinyl, 1,3,4-oxadiazolidinyl, 1,2,4-thiadiazolidinyl,1,3,4-thiadiazolidinyl, 1,2,4-triazolidinyl, 1,3,4-triazolidinyl,2,3-dihydrofuryl, 2,5-dihydrofuryl, 2,3-dihydrothienyl,2,5-dihydrothienyl, 2,3-pyrrolinyl, 2,5-pyrrolinyl, 2,3-isoxazolinyl,3,4-isoxazolinyl, 4,5-isoxazolinyl, 2,3-isothiazolinyl,3,4-isothiazolinyl, 4,5-isothiazolinyl, 2,3-dihydropyrazolyl,3,4-dihydropyrazolyl, 4,5-dihydropyrazolyl, 2,3-dihydrooxazolyl,3,4-dihydrooxazolyl, piperidinyl, tetrahydropyridazinyl,tetrahydropyrimidinyl, tetrahydropyrazinyl, 1,3,5-tetrahydrotriazinyland 1,2,4-tetrahydrotriazinyl,

and the following heteroaromatic compounds: furyl, such as 2-furyl and3-furyl, thienyl, such as 2-thienyl and 3-thienyl, pyrrolyl, such as2-pyrrolyl and 3-pyrrolyl, isoxazolyl, such as 3-isoxazolyl,4-isoxazolyl and 5-isoxazolyl, isothiazolyl, such as 3-isothiazolyl,4-isothiazolyl and 5-isothiazolyl, pyrazolyl, such as 3-pyrazolyl,4-pyrazolyl and 5-pyrazolyl, oxazolyl, such as 2-oxazolyl, 4-oxazolyland 5-oxazolyl, thiazolyl, such as 2-thiazolyl, 4-thiazolyl and5-thiazolyl, imidazolyl, such as 2-imidazolyl and 4-imidazolyl,oxadiazolyl, such as 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and1,3,4-oxadiazol-2-yl, thiadiazolyl, such as 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl and 1,3,4-thiadiazol-2-yl, triazolyl, such as1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl and 1,2,4-triazol-4-yl,pyridinyl, such as 2-pyridinyl, 3-pyridinyl and 4-pyridinyl,pyridazinyl, such as 3-pyridazinyl and 4-pyridazinyl, pyrimidinyl, suchas 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, furthermore2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, in particularpyridyl, pyrimidyl, furanyl and thienyl.

All phenyl and heterocyclic rings are preferably unsubstituted or haveattached to them a halogen, methyl, trifluoromethyl or methoxysubstituent.

With a view to the use of the compounds of the formula I according tothe invention as herbicides and/or as compounds with adefoliant/desiccant action, the variables preferably have the followingmeanings, and was [sic] in each case alone or in combination:

X is --N(R⁷)--O-- bonded to R⁸ via oxygen;

X is --O--N(R⁷)-- bonded to R⁸ via nitrogen;

Y is oxygen;

R¹ is halogen or cyano;

R² is hydrogen, fluorine or chlorine;

R³ is amino or methyl;

R⁴ is C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl or C₁ -C₆ -alkylsulfonyl,particularly preferably C₁ -C₄ -haloalkyl, in particulartrifluoromethyl, chlorodifluoromethyl or pentafluoroethyl;

R⁵ is hydrogen or halogen;

R⁶ is hydrogen or C₁ -C₄ -alkyl, particularly preferably hydrogen;

R⁷ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₈ -cycloalkyl, C₁ -C₆ -haloalkyl, C₃-C₆ -alkenyl, C₃ -C₆ -alkynyl, (C₁ -C₆ -alkyl)carbonyl, (C₃ -C₆-alkenyl)carbonyl, (C₃ -C₆ -alkynyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl,(C₂ -C₆ -alkenyloxy)carbonyl, (C₂ -C₆ -alkynyloxy)carbonyl, (C₁ -C₆-alkylthio)carbonyl, C₁ -C₆ -alkylcarbamoyl, it being possible, ifdesired, for each of the last-mentioned 13 radicals to have attached toit one or two substituents, in each case selected from the groupconsisting of

nitro, cyano, halogen, C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃-C₈ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆-alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy,

a group --CO--Z¹ R⁹, --OCO--Z¹ R⁹ or --N(R⁹)R¹⁰ ;

R⁸ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₈ -cycloalkyl, C₁ -C₆ -haloalkyl, C₃-C₆ -alkenyl or C₃ -C₆ -alkynyl, it being possible, if desired, for eachof the last-mentioned 5 radicals to have attached to it one or twosubstituents, in each case selected from the group consisting of

nitro, cyano, halogen, C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃-C₈ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆-alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy,

a group --CO--Z² R¹¹, --OCO--Z² R¹¹ or --N(R¹¹)R¹² ;

Z¹ is a chemical bond, oxygen, sulfur or --N(R¹⁰)--;

Z² is a chemical bond, oxygen, sulfur or --N(R¹²)--;

R⁹, R¹¹ independently of one another are hydrogen, C₁ -C₆ -alkyl, C₃ -C₈-cycloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl or (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl;

or

Z¹ and R⁹ and/or Z² and R¹¹ in each case together represent a 3- to7-membered heterocycle bonded via nitrogen which has one to three heteroatoms selected from the group consisting of two oxygen atoms, two sulfuratoms and 3 nitrogen atoms, it being possible for the heterocycle to besaturated, partially or fully unsaturated or aromatic and, if desired,to have attached to it one to three substituents, in each case selectedfrom the group consisting of nitro, cyano, halogen, C₁ -C₆ -alkyl, C₁-C₆ -haloalkyl and C₁ -C₆ -alkoxy;

R¹⁰, R¹² independently of one another are hydrogen or C₁ -C₆ -alkyl.

R⁷ is particularly preferably: hydrogen, C₁ -C₆ -alkyl, C₃ -C₈-cycloalkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, (C₁-C₆ -alkyl)carbonyl, (C₃ -C₆ -alkenyl)carbonyl, (C₃ -C₆-alkynyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl or C₁ -C₆ -alkylcarbamoyl,it being possible for each of the last-mentioned 10 radicalsadditionally to have attached to it one of the following substituents:nitro, cyano, halogen, C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃-C₈ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆-alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylsulfenyl [sic],C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy, a group --CO--Z¹ R⁹,--OCO--Z¹ R⁹ or --N(R⁹)R¹⁰.

R⁸ is particularly preferably: hydrogen, C₁ -C₆ -alkyl, C₃ -C₈-cycloalkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl or C₃ -C₆ -alkynyl, itbeing possible for each of the last-mentioned 5 radicals additionally tohave attached to it one of the following substituents: nitro, cyano,halogen, C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈-cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁-C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy, a group --CO--Z² R¹¹,--OCO--Z² R¹¹ or --N(R¹¹)R¹².

Very particularly preferred are the compounds Ia (= I where X=--NH--O--,Y=oxygen, R¹ =chlorine, R² =fluorine, R³ =amino, R⁴ =trifluoromethyl andR⁵, R⁶ =hydrogen) which are listed in Table 1 below:

                  TABLE 1                                                         ______________________________________                                                                       Ia                                                                              #STR5##                                         -                                                                          No.        R.sub.8                                                            ______________________________________                                        Ia.01      H                                                                    Ia.02      CH.sub.3                                                           Ia.03      C.sub.2 H.sub.5                                                    Ia.04      n-C.sub.3 H.sub.7                                                  Ia.05      i-C.sub.3 H.sub.7                                                  Ia.06      n-C.sub.4 H.sub.9                                                  Ia.07      i-C.sub.4 H.sub.9                                                  Ia.08      s-C.sub.4 H.sub.9                                                  Ia.09      tert-C.sub.4 H.sub.9                                               Ia.10      cyclopropyl                                                        Ia.11       cyclobutyl                                                        Ia.12       cyclopentyl                                                       Ia.13       cyclohexyl                                                        Ia.14       cycloheptyl                                                       Ia.15       cyclooctyl                                                        Ia.16       CH.sub.2 CN                                                       Ia.17       CH.sub.2 CH.sub.2 CN                                              Ia.18       CH(CH.sub.3)CN                                                    Ia.19       C(CH.sub.3).sub.2 CN                                              Ia.20       C(CH.sub.3).sub.2 CH.sub.2 CN                                     Ia.21       CH.sub.2 Cl                                                       Ia.22       CH.sub.2 CH.sub.2 Cl                                              Ia.23       CH(CH.sub.3)CH.sub.2 Cl                                           Ia.24       CH.sub.2 CF.sub.3                                                 Ia.25       CHCl.sub.2                                                        Ia.26       CF.sub.2 Cl                                                       Ia.27       CF.sub.3                                                          Ia.28       C.sub.2 F.sub.5                                                   Ia.29       CF.sub.2 H                                                        Ia.30       CH.sub.2 --CH═CH.sub.2                                        Ia.31       CH(CH.sub.3)CH═CH.sub.2                                       Ia.32       CH.sub.2 --CH═CH--CH.sub.3                                    Ia.33       CH.sub.2 --CCH                                                    Ia.34       CH(CH.sub.3)C.tbd.CH                                              Ia.35       C(CH.sub.3).sub.2 C.tbd.CH                                        Ia.36       CH.sub.2 -COOH                                                    Ia.37       CH.sub.2 --CO--OCH.sub.3                                          Ia.38       CH.sub.2 --CO--OC.sub.2 H.sub.5                                   Ia.39       CH.sub.2 --CO--O-(n-C.sub.3 H.sub.7)                              Ia.40       CH.sub.2 --CO--O-(i-C.sub.3 H.sub.7)                              Ia.41       CH(CH.sub.3)--CO--OCH.sub.3                                       Ia.42       CH(CH.sub.3)--CO--OC.sub.2 H.sub.5                                Ia.43       CH(CH.sub.3)--CO--O-(n-C.sub.3 H.sub.7)                           Ia.44       CH(CH.sub.3)--CO--O-(i-C.sub.3 H.sub.7)                           Ia.45       CH.sub.2 --COO--(CH.sub.2).sub.2 --OCH.sub.3                      Ia.46       CH2--COO--(CH.sub.2)2--OCH.sub.3                                  Ia.47       CH(CH.sub.3)--COO--(CH.sub.2).sub.2 --OCH.sub.3                   Ia.48       CH(CH.sub.3)--COO--(CH.sub.2).sub.2 --OC.sub.2 H.sub.5                      Ia.49       CH.sub.2 --CONH.sub.2                                   Ia.50       CH.sub.2 --CONHCH.sub.3                                           Ia.51       CH.sub.2 --CONHC.sub.2 H.sub.5                                    Ia.52       CH.sub.2 --CON(CH.sub.3).sub.2                                    Ia.53       CH(CH.sub.3)--CONH.sub.2                                          Ia.54       CH(CH.sub.3)--CONHCH.sub.3                                        Ia.55       CH(CH.sub.3)--CONH-cyclopropyl                                    Ia.56       CH(CH.sub.3)--CONHC.sub.2 H.sub.5                                 Ia.57       CH(CH.sub.3)--CON(CH.sub.3).sub.2                                 Ia.58       CH.sub.2 --SCH.sub.3                                              Ia.59       (CH.sub.2).sub.2 --SCH.sub.3                                      Ia.60       (CH.sub.2).sub.2 --SC.sub.2 H.sub.5                               Ia.61       (CH.sub.2).sub.2 --SO--CH.sub.3                                   Ia.62       (CH.sub.2).sub.2 --SO.sub.2 --CH.sub.3                            Ia.63       (CH.sub.2).sub.2 -cyclopropyl                                     Ia.64       (CH.sub.2).sub.2 -cyclopentyl                                     Ia.65       (CH.sub.2).sub.2 --O--N═C(CH.sub.3).sub.2                     Ia.66       (CH.sub.2).sub.3 --O--N═C(CH.sub.3).sub.2                     Ia.67       (CH.sub.2).sub.2 --NO.sub.2                                       Ia.68       (CH.sub.2).sub.2 --NH.sub.2                                       Ia.69       (CH.sub.2).sub.2 --NHCH.sub.3                                     Ia.70       (CH.sub.2).sub.2 --NH(CH.sub.3).sub.2                             Ia.71       CH.sub.2 --OCH.sub.3                                              Ia.72       CH(CH.sub.3)--OCH.sub.3                                           Ia.73       CH(CH.sub.3)--OC.sub.2 H.sub.5                                    Ia.74       CH(CH.sub.3)CH.sub.2 --OCH.sub.3                                  Ia.75       (CH.sub.2).sub.2 OH                                               Ia.76       CH.sub.2 --OC.sub.2 H.sub.5                                       Ia.77       CH.sub.2 CO--O--(4-acetoxytetrahydrofuranyl)                      Ia.78       CH.sub.2 --OCOCH.sub.3                                            Ia.79       CH.sub.2 --OCOC.sub.2 H.sub.5                                     Ia.80       CH.sub.2 --C.sub.6 H.sub.5                                        Ia.81       (CH.sub.2).sub.2 --C.sub.6 H.sub.5                                Ia.82       CH.sub.2 -(4-Cl--C.sub.6 H.sub.4)                                 Ia.83       CH.sub.2 -(4-CF.sub.3 --C.sub.6 H.sub.4)                          Ia.84       CH.sub.2 -(3-NO.sub.2 --C.sub.6 H.sub.4)                        ______________________________________                                    

Other very particularly preferred benzylhydroxylamines of the formula Iare those which follow:

the compounds Ib.01-Ib.84, which only differ from the correspondingcompounds Ia.01-Ia.84 by the fact that R¹ is cyano: ##STR6## thecompounds Ic.01-Ic.84, which only differ from the correspondingcompounds Ia.01-Ia.84 by the fact that R² is hydrogen: ##STR7## thecompounds Id.01-Id.84, which only differ from the correspondingcompounds Ia.01-Ia.84 by the fact that R¹ is cyano and R² is hydrogen:##STR8## the compounds Ie.01-Ie.84, which only differ from thecorresponding compounds Ia.01-Ia.84 by the fact that R³ is methyl:##STR9## the compounds If.01-If.84, which only differ from thecorresponding compounds Ia.01-Ia.84 by the fact that R¹ is cyano and R³is methyl: ##STR10## the compounds Ig.01-Ig.84, which only differ fromthe corresponding compounds Ia.01-Ia.84 by the fact that R² is hydrogenand R³ is methyl: ##STR11## the compounds Ih.01-Ih.84, which only differfrom the corresponding compounds Ia.01-Ia.84 by the fact that R¹ iscyano, R² is hydrogen and R³ is methyl: ##STR12##

Further very particularly preferred compounds are the compounds Ii (= Iwhere Y=oxygen, R¹ =chlorine, R² =fluorine, R³ =amino, R⁴=trifluoromethyl, R⁵ and R⁶ =hydrogen, R⁸ =methyl) which are listed inTable 2 below:

                  TABLE 2                                                         ______________________________________                                                                       Ii                                                                              #STR13##                                        -                                                                          No.      R.sup.7                                                              ______________________________________                                        Ii.01    CH.sub.3                                                               Ii.02     C.sub.2 H.sub.5                                                     Ii.03     n-C.sub.3 H.sub.7                                                   Ii.04     i-C.sub.3 H.sub.7                                                   Ii.05     n-C.sub.4 H.sub.9                                                   Ii.06     i-C.sub.4 H.sub.9                                                   Ii.07     s-C.sub.4 H.sub.9                                                   Ii.08     tert-C.sub.4 H.sub.9                                                Ii.09     cyclopropyl                                                         Ii.10     cyclobutyl                                                          Ii.11     cyclopentyl                                                         Ii.12     cyclohexyl                                                          Ii.13     cycloheptyl                                                         Ii.14     cyclooctyl                                                          Ii.15     CH.sub.2 CN                                                         Ii.16     CH.sub.2 CH.sub.2 CN                                                Ii.17     CH(CH.sub.3)CN                                                      Ii.18     C(CH.sub.3).sub.2 CN                                                Ii.19       C(CH.sub.3).sub.2 CH.sub.2 CN                                     Ii.20       CH.sub.2 Cl                                                       Ii.21       CH.sub.2 CH.sub.2 Cl                                              Ii.22       CH(CH.sub.3)CH.sub.2 Cl                                           Ii.23       CH.sub.2 CF.sub.3                                                 Ii.24       CH.sub.2 --CH═CH.sub.2                                        Ii.25       CH(CH.sub.3)CH═CH.sub.2                                       Ii.26       CH.sub.2 --CH═CH--CH.sub.3                                    Ii.27       CH.sub.2 --CCH                                                    Ii.28       CH(CH.sub.3)C.tbd.CH                                              Ii.29       C(CH.sub.3).sub.2 C.tbd.CH                                        Ii.30       CH.sub.2 --COOH                                                   Ii.31       CH.sub.2 --CO--OCH.sub.3                                          Ii.32       CH.sub.2 --CO--OC.sub.2 H.sub.5                                   Ii.33       CH.sub.2 --CO--O--(n-C.sub.3 H.sub.7)                             Ii.34       CH.sub.2 --CO-(i-C.sub.3 H.sub.7)                                 Ii.35       CH(CH.sub.3)--CO--OCH.sub.3                                       Ii.36       CH(CH.sub.3)--CO--OC.sub.2 H.sub.5                                Ii.37       CH(CH.sub.3)--CO--O-(n-C.sub.3 H.sub.7)                           Ii.38       CH(CH.sub.3)--CO--O-(i-C.sub.3 H.sub.7)                           Ii.39       CH.sub.2 --COO--(CH.sub.2).sub.2 --OCH.sub.3                      Ii.40       CH.sub.2 --COO--(CH.sub.2).sub.2 --OCH.sub.3                      Ii.41       CH(CH.sub.3)--COO--(CH.sub.2).sub.2 --OCH.sub.3                   Ii.42       CH(CH.sub.3)--COO--(CH.sub.2).sub.2 --OC.sub.2 H.sub.5                    Ii.43       CH.sub.2 --CONH.sub.2                                     Ii.44       CH.sub.2 --CONHCH.sub.3                                           Ii.45       CH.sub.2 --CONHC.sub.2 H.sub.5                                    Ii.46       CH.sub.2 --CON(CH.sub.3).sub.2                                    Ii.47       CH(CH.sub.3)--CONH.sub.2                                          Ii.48       CH(CH.sub.3)--CONHCH.sub.3                                        Ii.49       CH(CH.sub.3)--CONHC.sub.2 H.sub.5                                 Ii.50       CH(CH.sub.3)--CON(CH.sub.3).sub.2                                 Ii.51       CH.sub.2 --SCH.sub.3                                              Ii.52       (CH.sub.2).sub.2 --SCH.sub.3                                      Ii.53       (CH.sub.2).sub.2 --SC.sub.2 H.sub.5                               Ii.54       (CH.sub.2).sub.2 --SO--CH.sub.3                                   Ii.55       CH(CH.sub.3)--SO.sub.2 --CH.sub.3                                 Ii.56       (CH.sub.2).sub.2 --SO.sub.2 --CH.sub.3                            Ii.57       (CH.sub.2).sub.2 -cyclopropyl                                     Ii.58       (CH.sub.2).sub.2 -cyclopentyl                                     Ii.59       (CH.sub.2).sub.2 --O--N═C(CH.sub.3).sub.2                     Ii.60       (CH.sub.2).sub.3 --O--N═C(CH.sub.3).sub.2                     Ii.61       (CH.sub.2).sub.2 --NO.sub.2                                       Ii.62       (CH.sub.2).sub.2 --NH.sub.2                                       Ii.63       (CH.sub.2).sub.2 --NHCH.sub.3                                     Ii.64       (CH.sub.2).sub.2 --NH(CH.sub.3).sub.2                             Ii.65       CH.sub.2 --OCH.sub.3                                              Ii.66       CH(CH.sub.3)--OCH.sub.3                                           Ii.67       CH(CH.sub.3)--OC.sub.2 H.sub.5                                    Ii.68       CH(CH.sub.3)CH.sub.2 --OCH.sub.3                                  Ii.69       (CH.sub.2).sub.2 OH                                               Ii.70       CH.sub.2 --OC.sub.2 H.sub.5                                       Ii.71       CH.sub.2 CO--O--(4-acetoxytetrahydrofuran-3-yl)                   Ii.72       CH.sub.2 --OCOCH.sub.3                                            Ii.73       CH.sub.2 --OCOC.sub.2 H.sub.5                                     Ii.74       CH.sub.2 --C.sub.6 H.sub.5                                        Ii.75       (CH.sub.2).sub.2 --C.sub.6 H.sub.5                                Ii.76       COOH                                                              Ii.77       CO--O--CH.sub.3                                                   Ii.78       CO--O--C.sub.2 H.sub.5                                            Ii.79       CO--O-(n-C.sub.3 H.sub.7)                                         Ii.80       CO--O-(i-C.sub.3 H.sub.7)                                         Ii.81       CO--O-(n-C.sub.4 H.sub.9)                                         Ii.82       CO--O-(i-C.sub.4 H.sub.9)                                         Ii.83       CO--O-(s-C.sub.4 H.sub.9)                                         Ii.84       CO--O-(tert-C.sub.4 H.sub.9)                                      Ii.85       COO-cyclopropyl                                                   Ii.86       COO-cyclobutyl                                                    Ii.87       COO-cyclopentyl                                                   Ii.88       COO-cyclohexyl                                                    Ii.89       COO-cycloheptyl                                                   Ii.90       COO-cyclooctyl                                                    Ii.91       COO--CH.sub.2 CN                                                  Ii.92       COO--CH.sub.2 CH.sub.2 CN                                         Ii.93       COO--CH(CH.sub.3)CN                                               Ii.94       COO--C(CH.sub.3).sub.2 CN                                         Ii.95       COO--C(CH.sub.3).sub.2 CH.sub.2 CN                                Ii.96       COO--CH.sub.2 Cl                                                  Ii.97       COO--CH.sub.2 CH.sub.2 Cl                                         Ii.98       COO--CH(CH.sub.3)CH.sub.2 Cl                                      Ii.99       COO--CH.sub.2 CF.sub.3                                            Ii.100      COO--CHCl.sub.2                                                   Ii.101      COO--CF.sub.2 Cl                                                  Ii.102      COO--CF.sub.3                                                     Ii.103      COO--C.sub.2 F.sub.5                                              Ii.104      COO--CF.sub.2 H                                                   Ii.105      COO--CH.sub.2 --CH═CH.sub.2                                   Ii.106      COO--CH(CH.sub.3)CH═CH.sub.2                                  Ii.107      COO--CH.sub.2 --CH═CH--CH.sub.3                               Ii.108      COO--CH.sub.2 --C.tbd.CH                                          Ii.109      COO--CH(CH.sub.3)C.tbd.CH                                         Ii.110      COO--C(CH.sub.3).sub.2 C.tbd.CH                                   Ii.111      COO--CH.sub.2 --COOH                                              Ii.112      COO--CH.sub.2 --CO--OCH.sub.3                                     Ii.113      COO--CH.sub.2 --CO--OC.sub.2 H.sub.5                              Ii.114      COO--CH.sub.2 --CO--O-(n-C.sub.3 H.sub.7)                         Ii.115      COO--CH.sub.2 --CO--O-(i-C.sub.3 H.sub.7)                         Ii.116      COO--CH(CH.sub.3)--CO--OCH.sub.3                                  Ii.117      COO--CH(CH.sub.3)--CO--OC.sub.2 H.sub.5                           Ii.118      COO--CH(CH.sub.3)--CO--O-(n-C.sub.3 H.sub.7)                      Ii.119      COO--CH(CH.sub.3)--CO--O-(i-C.sub.3 H.sub.7)                      Ii.120      COO--CH.sub.2 --COO--(CH.sub.2).sub.2 --OCH.sub.3                 Ii.121      COO--CH.sub.2 --COO--(CH.sub.2).sub.2 --OCH.sub.3                 Ii.122      COO--CH(CH.sub.3)--COO--(CH.sub.2).sub.2 --OCH.sub.3                      Ii.123      COO--CH(CH.sub.3)--COO--(CH.sub.2).sub.2 --OC.sub.2              H.sub.5                                                                Ii.124      COO--CH.sub.2 --CONH.sub.2                                        Ii.125      COO--CH.sub.2 --CONHCH.sub.3                                      Ii.126      COO--CH.sub.2 --CONHC.sub.2 H.sub.5                               Ii.127      COO--CH.sub.2 --CON (CH.sub.3).sub.2                              Ii.128      COO--CH(CH.sub.3)--CONH.sub.2                                     Ii.129      COO--CH(CH.sub.3)--CONHCH.sub.3                                   Ii.130      COO--CH(CH.sub.3)--CONHC.sub.2 H.sub.5                            Ii.131      COO--CH(CH.sub.3)--CON(CH.sub.3).sub.2                            Ii.132      COO--CH.sub.2 --SCH.sub.3                                         Ii.133      COO--(CH.sub.2).sub.2 --SCH.sub.3                                 Ii.134      COO--(CH.sub.2).sub.2 --SC.sub.2 H.sub.5                          Ii.135      COO--(CH.sub.2).sub.2 --SO--CH.sub.3                              Ii.136      COO--(CH.sub.2).sub.2 --SO.sub.2 --CH.sub.3                       Ii.137      COO--(CH.sub.2).sub.2 --SO--CH.sub.3                              Ii.138      COO--(CH.sub.2).sub.2 -cyclopropyl                                Ii.139      COO--(CH.sub.2).sub.2 -cyclopentyl                                Ii.140      COO--(CH.sub.2).sub.2 --O--N═C(CH.sub.3).sub.2                Ii.141      COO--(CH.sub.2).sub.3 --O--N═C(CH.sub.3).sub.2                Ii.142      COO--(CH.sub.2).sub.2 --NO.sub.2                                  Ii.143      COO--(CH.sub.2).sub.2 --NH.sub.2                                  Ii.144      COO--(CH.sub.2).sub.2 --NHCH.sub.3                                Ii.145      COO--(CH.sub.2).sub.2 --NH(CH.sub.3).sub.2                        Ii.146      COO--CH.sub.2 --OCH.sub.3                                         Ii.147      COO--CH(CH.sub.3)--OCH.sub.3                                      Ii.148      COO--CH(CH.sub.3)--OC.sub.2 H.sub.5                               Ii.149      COO--CH(CH.sub.3)CH.sub.2 --OCH.sub.3                             Ii.150      COO--(CH.sub.2).sub.2 OH                                          Ii.151      COO--CH.sub.2 --OC.sub.2 H.sub.5                                  Ii.152    COO--CH.sub.2 CO--O-( 4-acetoxytetrahydrofuran-3-yl)                Ii.153    COO--CH.sub.2 --OCOCH.sub.3                                         Ii.154    COO--CH.sub.2 --OCOC.sub.2 H.sub.5                                  Ii.155    COO--CH.sub.2 --C.sub.6 H.sub.5                                     Ii.156    COO--(CH.sub.2).sub.2 --C.sub.6 H.sub.5                             Ii.157    COO--CH.sub.2 -(4-Cl--C.sub.6 H.sub.4)                              Ii.158    COO--CH.sub.2 -(4-CF.sub.3 --C.sub.6 H.sub.4)                       Ii.159    COO--CH.sub.2 -(3-NO.sub.2 --C.sub.6 H.sub.4)                       Ii.160    CHO                                                                 Ii.161    CO--CH.sub.3                                                        Ii.162    CO--C.sub.2 H.sub.5                                                 Ii.163    CO-(n-C.sub.3 H.sub.7)                                              Ii.164    CO-(i-C.sub.3 H.sub.7)                                              Ii.165    CO-(n-C.sub.4 H.sub.9)                                              Ii.166    CO-(i-C.sub.4 H.sub.9)                                              Ii.167    CO-(s-C.sub.4 H.sub.9)                                              Ii.168    CO-(tert-C.sub.4 H.sub.9)                                           Ii.169    CO-cyclopropyl                                                      Ii.170    CO-cyclobutyl                                                       Ii.171    CO-cyclopentyl                                                      Ii.172    CO-cyclohexyl                                                       Ii.173    CO-cycloheptyl                                                      Ii.174    CO-cyclooctyl                                                       Ii.175    CO--CH.sub.2 CN                                                     Ii.176    CO--CH.sub.2 CH.sub.2 CN                                            Ii.177    CO--CH(CH.sub.3)CN                                                  Ii.178    CO--C(CH.sub.3).sub.2 CN                                            Ii.179    CO--C(CH.sub.3).sub.2 CH.sub.2 CN                                   Ii.180    CO--CH.sub.2 Cl                                                     Ii.181     CO--CH.sub.2 CH.sub.2 Cl                                           Ii.182     CO--CH(CH.sub.3)CH.sub.2 Cl                                        Ii.183     CO--CH.sub.2 CF.sub.3                                              Ii.184     CO--CHCl.sub.2                                                     Ii.185     CO--CF.sub.2 Cl                                                    Ii.186     CO--CF.sub.3                                                       Ii.187     CO--C.sub.2 F.sub.5                                                Ii.188     CO--CF.sub.2 H                                                     Ii.189     CO--CH.sub.2 --CH═CH.sub.2                                     Ii.190     CO--CH(CH.sub.3)CH═CH.sub.2                                    Ii.191     CO--CH.sub.2 --CH═CH--CH.sub.3                                 Ii.192     CO--CH.sub.2 --C.tbd.CH                                            Ii.193     CO--CH(CH.sub.3)C.tbd.CH                                           Ii.194     CO--C(CH.sub.3).sub.2 C.tbd.CH                                     Ii.195     CO--CH.sub.2 --COOH                                                Ii.196     CO--CH.sub.2 --CO--OCH.sub.3                                       Ii.197     CO--CH.sub.2 --CO--OC.sub.2 H.sub.5                                Ii.198     CO--CH.sub.2 --CO--O-(n-C.sub.3 H.sub.7)                           Ii.199     CO--CH.sub.2 --CO--O-(i-C.sub.3 H.sub.7)                           Ii.200     CO--CH(CH.sub.3)--CO--OCH.sub.3                                    Ii.201     CO--CH (CH.sub.3)--CO--OC.sub.2 H.sub.5                            Ii.202     CO--CH(CH.sub.3)--CO--O-(n-C.sub.3 H.sub.7)                        Ii.203     CO--CH(CH.sub.3)--CO--O-(i-C.sub.3 H.sub.7)                        Ii.204     CO--CH.sub.2 --COO--(CH.sub.2).sub.2 --OCH.sub.3                   Ii.205     COCH.sub.2 --COO--(CH.sub.2).sub.2 --OCH.sub.3                     Ii.206     CO--CH(CH.sub.3)--COO--(CH.sub.2).sub.2 --OCH.sub.3                Ii.207     CO--CH(CH.sub.3)--COO--(CH.sub.2).sub.2 --OC.sub.2 H.sub.5                 Ii.208     CO--CH.sub.2 --CONH.sub.2                                  Ii.209     CO--CH.sub.2 --CONHCH.sub.3                                        Ii.210     CO--CH.sub.2 --CONHC.sub.2 H.sub.5                                 Ii.211     CO--CH.sub.2 --CON(CH.sub.3).sub.2                                 Ii.212     CO--CH(CH.sub.3)--CONH.sub.2                                       Ii.213     CO--CH(CH.sub.3)--CONHCH.sub.3                                     Ii.214     CO--CH(CH.sub.3)--CONHC.sub.2 H.sub.5                              Ii.215     CO--CH(CH.sub.3)--CON(CH.sub.3).sub.2                              Ii.216     CO--CH.sub.2 --SCH.sub.3                                           Ii.217     CO--(CH.sub.2).sub.2 --SCH.sub.3                                   Ii.218     CO--(CH.sub.2).sub.2 --SC.sub.2 H.sub.5                            Ii.219     CO--(CH.sub.2).sub.2 --SO--CH.sub.3                                Ii.220     CO--(CH.sub.2).sub.2 --SO.sub.2 --CH.sub.3                         Ii.221     CO--(CH.sub.2).sub.2 --SO--CH.sub.3                                Ii.222     CO--(CH.sub.2).sub.2 -cyclopropyl                                  Ii.223     CO--(CH.sub.2).sub.2 -cyclopentyl                                  Ii.224     CO--(CH.sub.2).sub.2 --O--N═C(CH.sub.3).sub.2                  Ii.225     CO--(CH.sub.2).sub.3 --O--N═C(CH.sub.3).sub.2                  Ii.226     CO--(CH.sub.2).sub.2 --NO.sub.2                                    Ii.227     CO--(CH.sub.2).sub.2 --NH.sub.2                                    Ii.228     CO--(CH.sub.2).sub.2 --NHCH.sub.3                                  Ii.229     CO--(CH.sub.2).sub.2 --NH(CH.sub.3).sub.2                          Ii.230     CO--CH.sub.2 --OCH.sub.3                                           Ii.231     CO--CH(CH.sub.3)--OCH.sub.3                                        Ii.232     CO--CH(CH.sub.3)--OC.sub.2 H.sub.5                                 Ii.233     CO--CH(CH.sub.3)CH.sub.2 --OCH.sub.3                               Ii.234     CO--(CH.sub.2).sub.2 OH                                            Ii.235     CO--CH.sub.2 --OC.sub.2 H.sub.5                                    Ii.236     CO--CH.sub.2 CO--O-(4-acetoxytetrahydrofuran-3-yl)                 Ii.237     CO--CH.sub.2 --OCOCH.sub.3                                         Ii.238     CO--CH.sub.2 --OCOC.sub.2 H.sub.5                                  Ii.239     CO--CH.sub.2 --C.sub.6 H.sub.5                                     Ii.240     CO--(CH.sub.2).sub.2 --C.sub.6 H.sub.5                             Ii.241     CO--CH.sub.2 -(4-Cl--C.sub.6 H.sub.4)                              Ii.242     CO--CH.sub.2 -(4-CF.sub.3 --C.sub.6 H.sub.4)                       Ii.243     CO--CH.sub.2 -(3-NO.sub.2 --C.sub.6 H.sub.4)                     ______________________________________                                    

Very particularly preferred benzylhydroxylamines I are also those whichfollow:

the compounds Ik.98-Ik.243, which only differ from the correspondingcompounds Ii.01-Ii.243 by the fact that R¹ is cyano: ##STR14## thecompounds Il.01-I1.243, which only differ from the correspondingcompounds Ii.01-Ii.243 by the fact that R² is hydrogen: ##STR15## thecompounds Im.01-Im.243, which only differ from the correspondingcompounds Ii.01-Ii.243 by the fact that R¹ is cyano and R² is hydrogen:##STR16## the compounds In.01-In.243, which only differ from thecorresponding compounds Ii.01-Ii.243 by the fact that R³ is methyl:##STR17## the compounds Io.01-Io.243, which only differ from thecorresponding compounds Ii.01-Ii.243 by the fact that R¹ is cyano and R³is methyl: ##STR18## the compounds Ip.01-Ip.243, which only differ fromthe corresponding compounds Ii.01-Ii.243 by the fact that R² is hydrogenand R³ is methyl: ##STR19## the compounds Iq.01-Iq.243, which onlydiffer from the corresponding compounds Ii.01-Ii.243 by the fact that R¹is cyano, R² is hydrogen and R³ is methyl: ##STR20##

Additionally very particularly preferred compounds Ir (= I whereY=oxygen, R¹ =chlorine, R³ =methyl, R⁴ =trifluoromethyl, R⁵ and R⁶=hydrogen) are those listed in Table 3 below:

                  TABLE 3                                                         ______________________________________                                                                       Ir                                                                              #STR21##                                        -                                                                          No.   R.sup.2                                                                              R.sup.7                  R.sup.8                                 ______________________________________                                        Ir.01 F      CH.sub.3                 H                                         Ir.02          F          C.sub.2 H.sub.5                            H                                             Ir.03          F          CH(CH.sub                                          .3).sub.2                        H                                             Ir.04          F          CH.sub.3                                           CH.sub.3                                  Ir.05          F          C.sub.2 H.sub.5                                                                         CH.sub.3                                  Ir.06          F          CO--CH.sub.3                          H                                                  Ir.07          F          CO--CH.su                                          b.3                                                                           CH.sub.3                                  Ir.08          F          CO--OCH.sub.3                         H                                                  Ir.09          F          CO--OCH.s                                          ub.3                                                                          CH.sub.3                                  Ir.10          F          CO--OC.sub.2 H.sub.5                       H                                             Ir.11          F          CO--OC.su                                          b.2 H.sub.5                                                                   CH.sub.3                                  Ir.12          F          CO--CH.sub.2 --CO--OC.sub.2 H.sub.5  H                                                   Ir.13          F          CO--CH.su                                          b.2 --CO--OC.sub.2 H.sub.5                                                    CH.sub.3                                  Ir.14          F          SO.sub.2 --CH.sub.3                        H                                             Ir.15          F          SO.sub.2                                           --CH.sub.3                                                                    CH.sub.3                                  Ir.16          F          CH.sub.2 --CO--OCH.sub.3                    H       Ir.17          F          CH.sub.2 --CO--OCH.sub.3                                                                CH.sub.3                                  Ir.18          F          CH.sub.2 --CH═C(Cl)--CO--OCH.sub.3 H                                                 Ir.19          F          CH.sub.2                                           --CH═C(Cl)--CO--OCH.sub.3                                                 CH.sub.3                                  Ir.20          F          CO--CH.sub.2 --CO--OCH.sub.2 --CH═CH.sub.2                                           H                                        Ir.21          F          CO--CH.sub.2 --CO--OCH.sub.2 --CH═CH.sub.2                                           CH.sub.3                                 Ir.22          F          CO--CH.sub.2 --CO--NH--CH.sub.3  H                  Ir.23          F          CO--CH.sub.2 --CO--N(CH.sub.3)--CH.sub.2                                                --CO--OCH.sub.3  H                        Ir.24          H          CH.sub.3                              H                                                  Ir.25          H          C.sub.2                                            H.sub.5                                                                       H                                         Ir.26          H          CH(CH.sub.3).sub.2                        H                                              Ir.27          H          CH.sub.3                                           CH.sub.3                                  Ir.28          H          C.sub.2 H.sub.5                                                                         CH.sub.3                                  Ir.29          H          CO--CH.sub.3                          H                                                  Ir.30          H          CO--CH.su                                          b.3                                                                           CH.sub.3                                  Ir.31          H          CO--OCH.sub.3                         H                                                  Ir.32          H          CO--OCH.s                                          ub.3                                                                          CH.sub.3                                  Ir.33          H          CO--OC.sub.2 H.sub.5                       H                                             Ir.34          H          CO--OC.su                                          b.2 H.sub.5                                                                   CH.sub.3                                  Ir.35          H          CO--CH.sub.2 --CO--OC.sub.2 H.sub.5  H                                                   Ir.36          H          CO--CH.su                                          b.2 --CO--OC.sub.2 H.sub.5                                                    CH.sub.3                                  Ir.37          H          SO.sub.2 --CH.sub.3                       H                                              Ir.38          H          SO.sub.2                                           --CH.sub.3                                                                    CH.sub.3                                  Ir.39          H          CH.sub.2 --CO--OCH.sub.3                  H                                              Ir.40          H          CH.sub.2                                           --CO--OCH.sub.3   CH.sub.3                Ir.41          H          CH.sub.2 --CH═C(Cl)--CO--OCH.sub.3                                                  H                                         Ir.42          H          CH.sub.2 --CH═C(Cl)--CO--OCH.sub.3                                                  CH.sub.3                                  Ir.43          H          CO--CH.sub.2 --CO--OCH.sub.2 --CH═CH.sub.2                                           H                                        Ir.44          H          CO--CH.sub.2 --CO--OCH.sub.2 --CH═CH.sub.2                                           CH.sub.3                                 Ir.45          H          CO--CH.sub.2 --CO--NH--CH.sub.3            H                                             Ir.46          H          CO--CH.su                                          b.2 --CO--N(CH.sub.3)--CH.sub.2                                               --CO--OCH.sub.3 H                       ______________________________________                                    

Finally, very particularly preferred benzylhydroxylamines I are alsothose which follow:

the compounds Is.01-Is.46, which only differ from the correspondingcompounds Ir.01-Ir.46 by the fact that R¹ is cyano: ##STR22## thecompounds It.01-It.46, which only differ from the correspondingcompounds Ir.01-Ir.46 by the fact that R³ is amino: ##STR23## thecompounds Iu.01-Iu.46, which only differ from the correspondingcompounds Ir.01-Ir.46 by the fact that R¹ is cyano and R³ is amino:##STR24##

The benzylhydroxylamines of the formula I can be obtained by variousroutes, for example by one of the following processes:

Process A

Cyclization of an enamine ester of the formula IV or of an enaminecarboxylate of the formula V in the presence of a base: ##STR25## L¹ islow-molecular-weight alkyl, preferably C₁ -C₄ -alkyl, or phenyl.

As a rule, the cyclization is carried out in an inert organic solvent ordiluent which is aprotic, for example in an aliphatic or cyclic ether,such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, in anaromatic, such as benzene and toluene, or in a polar solvent, such asdimethylformamide and dimethyl sulfoxide. Mixtures of polar solvent anda hydrocarbon, such as n-hexane, are also suitable. Depending on thestarting compound, water may also be suitable as the diluent.

Bases which are preferably suitable are alkali metal alcoholates, inparticular the sodium alcoholates, alkali metal hydroxides, inparticular sodium hydroxide and potassium hydroxide, alkali metalcarbonates, in particular sodium carbonate and potassium carbonate, andmetal hydrides, in particular sodium hydride. When using sodium hydrideas the base, it has proved advantageous to carry out the process in analiphatic or cyclic ether, in dimethylformamide or in dimethylsulfoxide.

0.5 to twice the molar amount of base based on the amount of IV or V isusually sufficient for successfully carrying out the reaction.

In general, the reaction temperature is from (-78)° C. to the boilingpoint of the reaction mixture in question, in particular at from (-60)to 60° C.

If R³ in formula IV or V is hydrogen, the process product is obtained asa metal salt, the metal corresponding to the cation of the base used.The salt can be isolated and purified in a manner known per se or, ifdesired, converted into the free compound I where R³ =hydrogen by meansof acid.

Process B

Methylation of a compound I where R³ is hydrogen in the presence of abase: ##STR26##

Examples of suitable methylating agents are methyl halides, preferablymethyl chloride, methyl iodide or methyl bromide, and also dimethylsulfate, methanesulfonate [sic] (methyl mesylate),methylbenzenesulfonate, methane-p-tolylsulfonate [sic] (methyltosylate), methane-p-bromobenzenesulfonate [sic] (methyl brosylate),methyl trifluoromethanesulfonate (methyltriflate) and diazomethane.

As a rule, the process is carried out in an inert organic solvent, forexample in a protic solvent, such as the lower alcohols, preferably inethanol, if desired as a mixture with water, or in an aprotic solvent,e.g. in an aliphatic or cyclic ether, preferably in 1,2-dimethoxyethane,tetrahydrofuran or dioxane, in an aliphatic ketone, preferably inacetone, in an amide, preferably in dimethylformamide, in a sulfoxide,preferably in dimethyl sulfoxide, in a urea, such as tetramethylurea,and 1,3-dimethyltetrahydro2(1H)-pyrimidinone [sic], in a carboxylicester, such as ethyl acetate, or in a halogenated aliphatic or aromatichydrocarbon, such as dichloromethane and chlorobenzene.

Suitable bases are inorganic bases, e.g. carbonates, such as sodiumcarbonate and potassium carbonate, hydrogen carbonates, such as sodiumhydrogen carbonate and potassium hydrogen carbonate, or alkali metalhydrides, such as sodium hydride and potassium hydride, and organicbases, e.g. amines, such as triethylamine, pyridine andN,N-diethylaniline, or alkali metal alcoholates, such as sodiummethanolate, sodium ethanolate and potassium tert-butanolate.

The amount of base and methylating agent is preferably in each case 0.5times to twice the molar amount based on the amount of startingcompound.

In general, the reaction temperature is from 0° C. up to the boilingpoint of the reaction mixture, in particular at from 0 to 60° C.

A preferred process variant consists in methylating the salt of I, whichhas been obtained by cyclizing IV (R³ =H) or V (R³ =H) in accordancewith process A), without isolation from the reaction mixture which canstill comprise excess base, e.g. sodium hydride, sodium alcoholate orsodium carbonate.

Unless they can be prepared directly by the cyclization described asmethod A) under alkaline conditions, the salts of those compounds Iwhere R³ is hydrogen can also be obtained in a manner known per se fromthe process products of method A). To this end, for example the aqueoussolution of an inorganic or organic base is treated with thebenzylhydroxylamine I where R³ is hydrogen. The salt is generally formedsufficiently rapidly at as little as 20-25° C.

It is particularly advantageous to prepare the sodium salt by dissolvingthe benzylhydroxylamine I (R³ =hydrogen) in aqueous sodium hydroxidesolution at 20-25° C., approximately equivalent amounts ofbenzylhydroxylamine and sodium hydroxide being employed. The salt of thebenzylhydroxylamine can then be isolated for example by precipitationwith a suitable inert solvent or by evaporation of the solvent.

Salts of the benzylhydroxylamines I (R³ =H) whose metal ion is not analkali metal ion can generally be prepared by double decomposition ofthe corresponding alkali metal salt in aqueous solution. Compounds whichcan be prepared in this manner are, for example, benzylhydroxylaminemetal salts which are insoluble in water.

Process C

Reaction of a benzylhydroxylamine of the formula I where R³ is hydrogenwith an electrophilic aminating reagent in the presence of a base:##STR27##

An aminating reagent which has proved particularly useful to date is2,4-dinitrophenoxyamine, but hydroxylamine-O-sulfonic acid (HOSA), whichhas already been disclosed in the literature as an aminating reagent(cf., for example, E. Hofer et al., Synthesis 1983, 466; W. Friedrichsenet al., Heterocycles 20 (1983) 1271; H. Hart et al., Tetrahedron Lett.25 (1984) 2073; B. Vercek et al., Monatsh. Chem. 114 (1983) 789; G.Sosnousky et al., Z. Naturforsch. 38 (1983) 884; R. S. Atkinson et al.,J. Chem. Soc. Perkin Trans. 1987, 2787), can, for example, also be used.

The amination can be carried out in a manner known per se (see, forexample, T. Sheradsky, Tetrahedron Lett. 1968, 1909; M. P. Wentland etal., J. Med. Chem. 27 (1984) 1103 and, in particular, EP-A 240 194, EP-A476 697, EP-A 517 181 and WO 95/06641, which teach the amination ofuracils).

The reaction is normally carried out in a polar solvent, e.g. indimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, or in ethylacetate, which has proved as particularly suitable to date.

Examples of suitable bases are alkali metal carbonates, such aspotassium carbonate, alkali metal alcoholates, such as sodium methylateand potassium tert-butanolate, or alkali metal hydrides, such as sodiumhydride.

The amount of base and aminating agent is preferably in each case 0.5times to twice the molar amount, based on the amount of startingcompound.

Depending on the meanings of R⁷ and R⁸, it may be necessary to protectthese substituents against amination in a manner known per se. This isparticularly to be recommended if R⁷ or R⁸ is hydrogen.

Process D

Sulfuration of a benzylhydroxylamine of the formula I where Y=oxygen:##STR28##

The sulfuration is generally carried out in an inert solvent or diluent,for example in an aromatic hydrocarbon such as toluene and the xylenes,in an ether, such as diethyl ether, 1,2-dimethoxyethane andtetrahydrofuran, or in an organic amine, such as pyridine.

Particularly suitable as sulfurating reagents are phosphorus(V) sulfideand 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-dithione("Lawesson reagent").

In general, 1 to 5 times the molar amount based on the starting compoundto be sulfurated is sufficient for an essentially complete reaction.

The reaction temperature is normally at from 20 to 200° C., preferablyat from 40° C. to the boiling point of the reaction mixture.

Process E

Alkylation or acylation of a benzylhydroxylamine of the formula I whereR⁷ is hydrogen in the presence of a base: ##STR29##

The alkylation can be carried out for example with the halide,preferably the chloride or bromide, the sulfate, sulfonate, preferablythe methanesulfonate (mesylate), benzenesulfonate, p-toluenesulfonate(tosylate), p-bromobenzenesulfonate (brosylate), thetrifluoromethanesulfonate (triflat) or the diazo compound of anunsubstituted or substituted alkane, cycloalkane, haloalkane, alkene oralkyne.

Suitable acylating agents are, e.g., the acid halides, in particular theacid chlorides, the anhydrides, isocyanates and sulfonyl chlorides ofsubstituted or unsubstituted alkane-, cycloalkane-, alkene-, alkyne- orphenylcarboxylic acids. Alternatively, the free acids or theiranhydrides are suitable if the process is then carried out in thepresence of a condensing agent, such as carbonyl diimidazole anddicyclohexylcarbodiimide.

The process is usually carried out in an inert organic solvent,preferably in an aprotic solvent, e.g. an aliphatic or cyclic ether,such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, an aliphaticketone, such as acetone, an amide, such as dimethylformamide, asulfoxide, such as dimethyl sulfoxide, a urea, such as tetramethylureaand 1,3-dimethyltetrahydro-2(1H)-pyrimidinone, a carboxylic ester, suchas ethyl acetate, or a halogenated aliphatic or aromatic hydrocarbon,such as dichloromethane, and chlorobenzene.

Suitable bases are inorganic bases, e.g. alkali metal carbonates, suchas sodium carbonate and potassium carbonate, alkali metal hydrogencarbonates, such as sodium hydrogen carbonate and potassium hydrogencarbonate, or alkali metal hydrides, such as sodium hydride andpotassium hydride, but also organic bases, e.g. amines, such astriethylamine, pyridine and N,N-diethylaniline, or alkali metalalcoholates, such as sodium methanolate, sodium ethanolate and potassiumtert-butanolate.

The amount of base and alkylating agent is preferably 0.5 times to twicethe molar amount based on the amount of I where R⁷ =hydrogen.

In general, a reaction temperature of from 0° C. to the boiling point ofthe reaction mixture, in particular from 0 to 60° C., is recommended.

Problems in connection with regioselectivity which may occur in the caseof starting compounds where R³ =hydrogen can be avoided in a mannerknown per se (use of 2 equivalents of base, introduction of a protectivegroup, and the like).

Process F

Reduction of an oximino compound of the formula VII: ##STR30##

Examples of suitable reducing agents are hydrides, such as boranecomplexes, e.g. borane-dimethyl sulfide or borane-pyridine complexes,moreover silanes, such as triethylsilane and diphenylmethylsilane, ormolecular hydrogen using a catalyst, such as platinum-on-charcoal.

If hydrogen is used, it is recommended to carry out the reaction underacidic conditions, e.g. in an organic or inorganic acid as the solvent.

The hydrogen pressure is generally at from atmospheric pressure to asuperatmospheric pressure of approximately 10 bar.

In general, the reduction is successfully carried out at from (-5) to+50° C.

The amount of reducing agent is not critical. The process can be carriedout with a smaller amount of reducing agent based on the amount of VIIor else with an excess, approximately up to 15 times the molar amount.0.5 times to twice the molar amount of reducing agent based on theoximino compound VII is preferably used.

Process G

Cleavage of an alkylideneaminoxy compound of the formula VIII: ##STR31##

The cleavage is expediently carried out using a Br.o slashed.nsted acidas catalyst. Normally, 0.5-2 times the molar amount of acid based on theamount of VIII will suffice. Suitable examples of acids are organicacids such as acetic acid and inorganic acids such as sulfuric acid andhydrochloric acid.

The reaction can be carried out directly in the acid or in an inertsolvent, eg. in toluene.

The cleavage is advantageously carried out in the presence of an oximesuch as hydroxylamine and methylhydroxylamine, in which case the oximeis employed in approximately equimolar amounts or in an excess of up to20 times the molar amount based on the amount of VIII. In general, areaction temperature of from 0° C. to the boiling point of the reactionmixture is recommended.

The alkylideneaminoxy compounds VIII can be obtained, in turn, forexample from benzyl derivatives IX: ##STR32##

As a rule, the reaction is carried out in an inert solvent/diluent withthe desired alkylideneaminohydroxide HO--N═C(R^(a),R^(b)). If IX isemployed as the benzyl halide (IXa), it is expedient to carry out theprocess in the presence of an organic base such as triethylamine or ofan inorganic base such as sodium carbonate and potassium carbonate. If,in contrast, a benzyl alcohol (IXb) is used as starting material, acondensing auxiliary such as carbodiimidazole is required.

Examples of suitable solvents are aromatics such as toluene and xylenes,esters such as ethyl acetate, ethers such as diethyl ether andtetrahydrofuran, halogenated aliphatics such as methylene chloride orbasic solvents such as pyridine and dimethylformamide.

IX and alkylideneaminohydroxide are expediently employed inapproximately stoichiometric amounts, or else the process is carried outusing a slight excess of one or the other reactant of up toapproximately 10 mol %.

In general, the reaction is carried out at from 0° C. to the boilingpoint of the reaction mixture.

Process H

Reaction of benzyl alcohols IXa with hydroxylamines HO--N(R⁷)--R⁸ :##STR33##

The process is preferably carried out in the presence of a condensingauxiliary such as carbodiimidazole in amounts of, normally, 0.5 to 2times the molar amount based on the amount of IXa.

As a rule, the reaction is carried out in an inert organic solvent, eg.a hydrocarbon such as toluene and the xylenes, an ester such as ethylacetate or an ether such as diethyl ether and tetrahydrofuran.

IX and Xa are expediently employed in approximately stoichiometricamounts, or else a slight excess of one or the other reactant of up toapproximately 10 mol % is used.

In general, a reaction temperature of from 0° C. to the boiling point ofthe reaction mixture is recommended.

Process K

Halogenation of a benzylhydroxylamine of the formula I where R⁵ ishydrogen: ##STR34##

The halogenation is generally carried out in an inert organic solvent ordiluent. Suitable agents for the chlorination and bromination are, forexample, aliphatic carboxylic acids, such as acetic acid, or chlorinatedaliphatic hydrocarbons such as methylene chloride, chloroform and carbontetrachloride.

Particularly preferred for the iodination are low-boiling aliphaticcarboxylic acids, such as acetic acid.

Particularly suitable agents for the chlorination and bromination areelemental chlorine or bromine, or else sulfuryl chloride or sulfurylbromide, at a reaction temperature of, preferably, from 0 to 60° C., inparticular from 10 to 30° C.

If desired, the chlorination and bromination can be carried out in thepresence of an acid-binding agent, particularly preferred agents beingsodium acetate and tertiary amines such as triethylamine,dimethylaniline and pyridine.

Particularly preferred as iodinating agent is elemental iodine, thereaction temperature in this case being from approximately 0 to 110° C.,preferably at from 10 to 30° C.

The iodination proceeds particularly advantageously in the presence of amineral acid, such as fuming nitric acid.

The amount of halogenating agent is not critical; usually, equimolaramounts of halogenating agent or an excess of up to approximately 200mol % based on the starting compound (I where R⁵ =hydrogen) are used.

Excess iodine can be removed for example, after the reaction by means ofsaturated aqueous sodium hydrogen sulfite solution.

Process L

Alkylation of a hydroxylamine or of a hydroxamic acid with a benzylhalide or benzyl alcohol derivative of the formula XI in the presence ofa base: ##STR35## L² is halogen or lower-alkylsulfonate,lower-haloalkylsulfonate or phenylsulfonate, which may be substituted.

As a rule, the process is carried out in an inert organic solvent,suitable solvents being, in particular, aprotic solvents, e.g. aliphaticor cyclic ethers, such as, preferably, 1,2-dimethoxyethane,tetrahydrofuran and dioxane, aliphatic ketones, such as, preferably,acetone, amides such as, preferably, dimethylformamide, sulfoxides suchas, preferably, dimethyl sulfoxide, ureas such as tetramethylurea and1,3-dimethyltetrahydro-2(1H)-pyrimidinone, carboxylic esters such asethyl acetate, or halogenated aliphatic or aromatic hydrocarbons, suchas dichloromethane and chlorobenzene.

Suitable bases are inorganic bases, e.g. carbonates, such as the alkalimetal carbonates, in particular sodium carbonate and potassiumcarbonate, hydrogen carbonates, such as the alkali metal hydrogencarbonates, in particular sodium hydrogen carbonate and potassiumhydrogen carbonate, or alkali metal hydride, such as sodium hydride andpotassium hydride, but also organic bases, e.g. amines, such astriethylamine, pyridine and N,N-diethylaniline, or alkali metalalcoholates, such as sodium methanolate, sodium ethanolate and potassiumtert-butanolate.

The amounts of base and alkylating agent XI are normally in each case0.5 times to twice the molar amount based on the amount of X.

In general, the reaction is carried out at from (-78)° C. to the boilingpoint of the reaction mixture, in particular at from (-60) to 60° C.

The enamine esters of the formula IV are novel. They can be prepared bymethods known per se, for example by one of the following processes:##STR36##

The process is preferably carried out under essentially anhydrousconditions in an inert solvent or diluent, particularly preferably inthe presence of an acidic or alkaline catalyst.

Suitable solvents or diluents are, in particular, organic solvents whichform an azeotropic mixture with water, for example aromatics such asbenzene, toluene and xylenes, halogenated hydrocarbons, such asmethylene chloride, chloroform, carbon tetrachloride and chlorobenzene,aliphatic and cyclic ethers, such as 1,2-dimethoxyethane,tetrahydrofuran and dioxane, or cyclohexane, but also alcohols, such asmethanol and ethanol.

Acidic catalysts which are preferably suitable are strong mineral acidssuch as sulfuric acid and hydrochloric acid, phosphorus-containingacids, such as orthophosphoric acid and polyphosphoric acid, organicacids such as p-toluenesulfonic acid, and acidic cation exchangers suchas "Amberlyst 15" (by Fluka).

Suitable basic catalysts are, e.g., metal hydrides, such as sodiumhydride, and, particularly preferably, metal alcoholates, such as sodiummethanolate and ethanolate.

XIII and the β-ketoester XII are expediently employed in approximatelystoichiometric amounts, or else the process is carried out with a slightexcess of one or the other component, up to approximately 10 mol %.

0.5 times to twice the molar amount of catalyst based on the amount ofone of the starting compounds is usually sufficient.

In general, the reaction is carried out at from 60 to 120° C.,preferably at the boiling point of the reaction mixture to rapidlyremove the water which forms.

N ##STR37## L³ is C₁ -C₄ -alkyl or phenyl.

This reaction can be carried out for example in an inert organic solventwhich is miscible with water, for example in an aliphatic or cyclicether, such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or alower alcohol, in particular ethanol, the reaction temperature usuallybeing at from 50 to 100° C., preferably at the boiling point of thereaction mixture.

However, the reaction can also be carried out in an aromatic diluentsuch as benzene, toluene and xylenes, in which case an addition ofeither an acidic catalyst, such as hydrochloric acid andp-toluenesulfonic acid, or of a base, e.g. an alkali metal alcoholate,such as sodium methanolate and sodium ethanolate, is advisable. In thisprocess variant, again, the reaction temperature is usually at from 50to 100° C., but preferably at from 60 to 80° C. As regards thequantities, the information given for method M) also applies here.

O ##STR38##

The reaction is expediently carried out in the presence of anessentially anhydrous aprotic organic solvent or diluent, for example analiphatic or cyclic ether, such as diethyl ether, 1,2-dimethoxyethane,tetrahydrofuran and dioxane, an aliphatic or aromatic hydrocarbon, suchas n-hexane, benzene, toluene and xylene, a halogenated, aliphatichydrocarbon, such as methylene chloride, chloroform, carbontetrachloride, 1,2-dichloroethane and chlorobenzene, an aprotic, polarsolvent, such as dimethylformamide, hexamethylphosphoric triamide anddimethyl sulfoxide, or a mixture of these.

If desired, the process can also be carried out in the presence of ametal hydride base, such as sodium hydride and potassium hydride, analkali metal alcoholate or alkaline earth metal alcoholate, such assodium methanolate, sodium ethanolate and potassium tert-butanolate, oran organic tertiary base, such as triethylamine and pyridine, it beingpossible for the organic base to act simultaneously as the solvent.

It is expedient to employ the starting compounds in stoichiometricamounts, or else to use a small excess of one or the other component ofup to approximately 10 mol %. If the process is carried out withoutsolvent in the presence of an organic base, it is recommended to employa substantial excess of the latter.

A reaction temperature of from (-80) to 50° C., in particular (-60) to30° C., is usually sufficient.

In a particularly preferred embodiment, the resulting enamine ester IVis converted directly (i.e. "in situ") into the corresponding desiredproduct I in accordance with process A) using an excess of base. Anyby-products (e.g. C-alkylation products in the case of compounds whereR⁵ =hydrogen) can be removed by means of conventional separationprocesses, such as crystallization and chromatography.

P ##STR39## L⁴ is C₁ -C₄ -alkyl or phenyl.

This reaction is expediently carried out in an aprotic, polar solvent ordiluent, such as dimethylformamide, 2-butanone, dimethyl sulfoxide andacetonitrile, advantageously in the presence of a base, for example analkali metal alcoholate or alkaline earth metal alcoholate, inparticular a sodium alkanolate, such as sodium methanolate, an alkalimetal carbonate or alkaline earth metal carbonate, in particular sodiumcarbonate, or an alkali metal hydride, such as lithium hydride andsodium hydride. 0.5 times to twice the molar amount of base, based onthe amount of XV or XVII, is usually sufficient.

The reaction temperature is generally at from 80 to 180° C., preferablyat the boiling point of the reaction mixture.

With regard to the ratios of the starting compounds, the informationgiven for method M) applies.

In a particularly preferred embodiment, a sodium alcoholate is used asthe base, and the alcohol which is formed in the course of the reactionis distilled off continuously. The enamine esters IV which are preparedin this manner can be cyclized from the reaction mixture withoutisolation in accordance with process A) to give a salt of thecorresponding benzylhydroxylamine I.

Q ##STR40##

This reaction is expediently carried out in an essentially anhydrousaprotic organic solvent or diluent, for example in the presence of analiphatic or cyclic ether, such as diethyl ether, 1,2-dimethoxyethane,tetrahydrofuran and dioxane, an aliphatic or aromatic hydrocarbon, suchas n-hexane, benzene, toluene and the xylenes, a halogenated, aliphatichydrocarbon, such as methylene chloride, chloroform, carbontetrachloride, 1,2-dichloroethane and chlorobenzene, an aprotic, polarsolvent, such as dimethylformamide, hexamethylphosphoric triamide anddimethyl sulfoxide, or a mixture of these.

If desired, the process can also be carried out in the presence of ametal hydride base, such as sodium hydride and potassium hydride, analkali metal alcoholate or alkaline earth metal alcoholate, such assodium methanolate, sodium ethanolate and potassium tert-butanolate, oran organic nitrogen base, such as triethylamine and pyridine, it beingpossible for the organic base to act simultaneously as the solvent.

It is expedient to employ the starting compounds in stoichiometricamounts or to use one of the components in an excess of up toapproximately 20 mol %. If the process is carried out without solvent inthe presence of an organic base, it is advantageous to use the latter inan even larger excess.

The reaction temperature is generally at from (-80) to 150° C.,preferably at from (-30)° C. to the boiling point of the reactionmixture in question.

The enamine carboxylates of the formula V are also novel; they too canbe prepared in a manner known per se, for example from an anilinederivative of the formula XV in accordance with the following reactionscheme R): ##STR41##

The reaction of XX with XIX is preferably carried out in an anhydrousinert aprotic solvent, for example in a halogenated hydrocarbon, such asmethylene chloride, chloroform, carbon tetrachloride and chlorobenzene,an aromatic hydrocarbon, such as benzene, toluene and the xylenes, or analiphatic or cyclic ether, such as diethyl ether, dibutyl ether,1,2-dimethoxyethane, tetrahydrofuran and dioxane.

The reaction temperature for this reaction (of XX with XIX) is generallyat from approximately 70 to 140° C., in particular 100 to 120° C.

The reaction of XII with XIX is an aminolysis, which is generallycarried out either in the absence of a solvent [cf., for example, J.Soc. Dyes Col. 42, 81 (1926), Ber. 64, 970 (1931); Org. Synth., Coll.Vol. IV, 80 (1963) and J. Am. Chem. Soc. 70, 2402 (1948)] or in an inertanhydrous solvent/diluent, in particular in an aprotic solvent, forexample in an aromatic, such as toluene and the xylenes, or ahalogenated aromatic, such as chlorobenzene.

It is recommended to carry out the process in the presence of analkaline catalyst, for example a higher-boiling amine [see, for example,Helv. Chim. Acta 11, 779 (1928) and U.S. Pat. No. 2,416,738] orpyridine.

The reaction temperature is preferably at from approximately 20 to 160°C.

The starting compounds are in each case expediently employed inapproximately stoichiometric amounts, or else the process is carried outwith a small excess of one or the other component of up to approximately10 mol %. If the process is carried out in the presence of an alkalinecatalyst, 0.5 times to twice the molar amount of catalyst based on theamount of one of the educts is generally sufficient.

The subsequent reaction of the resulting compounds of the formula XXIwith the amine HN(R³)--COOL¹ is advantageously carried out in anessentially anhydrous solvent/diluent under atmospheric pressure,particularly preferably in the presence of an acidic catalyst.

To prepare enamine carboxylates V where R³ =amino, it is recommended toemploy compounds XXII with a protected amino group (e.g. as ahydrazone).

Suitable solvents/diluents are, in particular, organic liquids which canbe mixed with water to give an azeotropic mixture, for examplearomatics, such as benzene, toluene and the xylenes, or halogenatedhydrocarbons, such as carbon tetrachloride and chlorobenzene.

Suitable catalysts are, in particular, strong mineral acids, such assulfuric acid, organic acids, such as p-toluenesulfonic acid,phorphorus-containing acids, such as orthophosphoric acid andpolyphosphoric acid, or acidic cation exchangers, such as "Amberlyst 15"(by Fluka).

The reaction temperature is generally at from approximately 70 to 150°C.; however, to rapidly remove the resulting reaction water, the processis expediently carried out at the boiling point of the reaction mixturein question.

The compounds of the formulae XIII, XVI, XVII and XXI are also novel.They too can be prepared in a manner known per se, particularlyadvantageously from the compounds of the formula XIX:

S): "Phosgenation" of Compounds of the formula XIX and hydrolysis of theprocess products XVI using ammonia (derivatives): ##STR42##

The process can be carried out in an inert essentially anhydroussolvent/diluent or in the absence of a solvent. The amino group ispreferably converted into the isocyanate group by means of phosgene ortrichloromethyl chloroformate.

Suitable solvents/diluents are, in particular, aprotic organic solvents,for example aromatics, such as toluene and the xylenes, halogenatedhydrocarbons, such as methylene chloride, chloroform, 1,2-dichloroethaneand chlorobenzene, aliphatic or cyclic ethers, such as1,2-dimethoxyethane, tetrahydrofuran and dioxane, esters, such as ethylacetate, and mixtures of these.

Depending on the aniline derivative XIX employed, it may be advantageousto add a base such as triethylamine, for example in 0.5 to twice themolar amount based on the amount of XIX.

The phenyl isocyanates XVI are usually formed at from 50° C. to theboiling point of the reaction mixture; they can subsequently be reactedwith ammonia or with a reactive ammonia derivative to give thephenylurea derivatives XIII.

T): Reaction with alkali metal cyanates: ##STR43##

M⁺ is the equivalent of a metal ion, in particular an alkali metal ion,such as sodium and potassium.

The reaction is generally carried out in an inert solvent/diluent, forexample in an aromatic hydrocarbon, such as toluene and the xylenes, inan aliphatic or cyclic ether, such as tetrahydrofuran and dioxane, in alower alcohol, such as methanol and ethanol, in water, or in a mixtureof these.

The amount of cyanate is not critical; however, at least equivalentamounts of aniline compound XIX and cyanate are required for a completereaction; however, an excess of cyanate of up to approximately 100 mol %may also be advantageous.

The reaction temperature is generally at from 0° C. to the boiling pointof the reaction mixture.

U): Reactions with esters L⁴ O--CO--L⁵ ##STR44##

L⁵ is halogen, preferably chlorine or bromine, C₁ -C₄ -alkoxy orphenoxy.

Suitable solvents/diluents are, for example, aromatic hydrocarbons, suchas toluene and the xylenes, halogenated hydrocarbons, such as methylenechloride, chloroform, 1,2-dichloroethane and chlorobenzene, aliphatic orcyclic ethers, such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane,esters, such as ethyl acetate, alcohols, such as methanol and ethanol,or water. Mixtures of an organic solvent and water are also suitable.

The process is preferably carried out in the presence of a base, e.g. inthe presence of an alkali metal hydroxide, alkali metal carbonate oralkali metal alcoholate, such as sodium hydroxide, sodium carbonate,sodium methanolate and sodium ethanolate, or of a tertiary amine, suchas pyridine and triethylamine.

If desired, a catalyst, e.g. a Lewis acid, such as antimony trichloride,may also be added.

The starting compounds and the base are expediently employed inapproximately stoichiometric amounts, but one or the other component mayalso be present in an excess of up to approximately 100 mol %.

The amount of catalyst is generally 1 to 50 mol %, preferably 2 to 30mol %, based on the amount of aniline compound XIX employed.

The reaction is usually successfully carried out at from (-40)° C. tothe boiling point of the reaction mixture.

The aniline compounds of the formula XIX are also novel. They areusually synthesized from the corresponding nitro compounds XXIII bymeans of hydrogenation or from anilines of the formula XXIV, which canbe converted into the corresponding aniline compounds of the formula XIXin accordance with process F): ##STR45##

The nitro compounds of the formula XXIII, too, are novel. They can besynthesized by processes known per se, for example by nitration of thecorresponding benzylamines.

The compounds of the formula VII, X, XI, XII, XIV, XV, XVIII, XIX andXXIV are known or can be synthesized in a manner known per se (cf., forexample, WO 92/02088 and DE-A 42 37 920).

Unless otherwise indicated, all processes described above areexpediently carried out under atmospheric pressure or under the inherentpressure of the reaction mixture in question.

Depending on the substitution pattern of the target compounds, it may beadvisable to change the sequence of individual reaction steps so thatcertain by-products are not formed, or are formed in smaller amounts.

The reaction mixtures are generally worked up by methods known per se,for example by removing the solvent, partitioning the residue in amixture of water and a suitable organic solvent, and working up theorganic phase to obtain the product.

The benzylhydroxylamines of the formula I may contain one or more chiralcenters and are then usually obtained in the form of enantiomer ordiastereomer mixtures, unless the synthesis is tailored to yield oneparticular isomer. If desired, the mixtures can be separated by themethods customary for this purpose, for example by means ofcrystallization or chromatography on an optically active adsorbate, togive the essentially pure isomers. Pure optically active isomers can,for example, also be prepared from corresponding, optically activestarting materials.

Benzylhydroxylamines I where R³, R⁷ or R⁸ are hydrogen can be convertedinto their salts, preferably their alkali metal salts, in a manner knownper se.

Salts of I whose metal ion is not an alkali metal ion can be prepared inthe customary manner by double decomposition of the corresponding alkalisalt, and ammonium, phosphonium, sulfonium and sulfoxonium salts bymeans of ammonia, phosphonium hydroxide, sulfonium hydroxide orsulfoxonium hydroxide.

The compounds I and their agriculturally useful salts, both in the formof isomer mixtures and in the form of the pure isomers, are suitable asherbicides. The herbicidal compositions comprising I effect very goodvegetation control on non-crop areas, particularly at high applicationrates. They act against broad-leaved weeds and grass weeds in crops suchas wheat, rice, maize, soya and cotton, without adversely affecting thecrop plants to a substantial extent. This effect is particularlypronounced at low rates of application.

Depending on the application method in question, the compounds I, or theherbicidal compositions comprising them, can also be employed in anumber of other crop plants for eliminating undesirable plants. Suitablecrops are, for example, the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spp. [sic] altissima, Beta vulgaris spp. [sic] rapa,Brassica napus var. napus, Brassica napus var. napobrassica, Brassicarapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus ssp., Manihot esculenta,Medicago sativa, Musa spp., Nicotiana tabacum (N.rustica), Oleaeuropaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Piceaabies, Pinus spp., Pisum sativum, Prunus avium, Prunus persica, Pyruscommunis, Ribes sylvestre, Ricinus communis, Saccharum officinarum,Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare),Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum,Vicia faba, Vitis vinifera und Zea mays.

Moreover, the compounds I can also be used in crops which tolerate theaction of herbicides as a result of breeding, including geneticengineering methods.

Furthermore, the benzylhydroxylamines I are also suitable for thedesiccation and/or defoliation of plants.

As desiccants, they are particularly suitable for desiccating the aerialparts of crop plants such as potatoes, oilseed rape, sunflowers and soyabeans. This allows completely mechanical harvesting of these importantcrop plants.

Also of economical interest is facilitating harvesting, which is madepossible by concentrating, in the course of time, dehiscence or reducingthe adhesion to the tree in the case of citrus fruit, olives or otherspecies and varieties of pomaceous fruit, stone fruit and hard-shelledfruit. The same mechanism, i.e. promotion of the formation of abscissiontissue between fruits or leaves and the shoot of the plants is alsoessential for the targeted defoliation of useful plants, in particularcotton.

Moreover, the reduced period of time within which the individual cottonplants mature results in better fiber quality post-harvest.

The compounds I, or the compositions comprising them, can be applied,for example, in the form of directly sprayable aqueous solutions,powders, suspensions, also highly concentrated aqueous, oily or othersuspensions or dispersions, emulsions, oil dispersions, pastes, dusts,spreading materials or granules, by means of spraying, atomizing,dusting, scattering or pouring. The use forms depend on the intendedpurposes; in any case, they should guarantee the finest possibledistribution of the active ingredients according to the invention.

Suitable inert auxiliaries for the preparation of directly sprayablesolutions, emulsions, pastes or oil dispersions are, mainly, mineral oilfractions of medium to high boiling point, such as kerosene and dieseloil, furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffins,tetrahydronaphthalene, alkylated naphthalenes or their derivatives,alkylated benzenes and their derivatives, alcohols, such as methanol,ethanol, propanol, butanol and cyclohexanol, ketones, such ascyclohexanone, strongly polar solvents, e.g. amines, such asN-methylpyrrolidone and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thesubstrates [sic], either as such or dissolved in an oil or solvent, canbe homogenized in water by means of a wetting agent, tackifier,dispersant or emulsifier. Alternatively, it is possible to prepareconcentrates comprising active ingredient, wetting agent, tackifier,dispersant or emulsifier, and, if desired, solvent or oil, and theseconcentrates are suitable for dilution with water.

Suitable surfactants (adjuvants) are the alkali metal salts, alkalineearth metal salts and ammonium salts of aromatic sulfonic acids, e.g.ligninsulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid anddibutylnaphthalenesulfonic acid, or of fatty acids, alkyl- andalkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, andsalts of sulfated hexa-, hepta- and octadecanols, and also of fattyalcohol glycol ether [sic], condensates of sulfonated naphthalene andits derivatives with formaldehyde, condensates of naphthalene or of thenaphthalenesulfonic acid with phenol and formaldehyde, olyoxyethyleneoctylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol,alkylphenyl polyglycol ethers, tributylphenyl olyglycol ether, alkylarylpolyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxidecondensates, ethoxylated castor oil, polyoxyethylene alkyl ethers orpolyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate,sorbitol esters, lignosulfite waste liquors or methylcellulose.

Powders, spreading materials and dusts can be prepared by mixing orconcomitantly grinding the active ingredients with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active ingredients to solidcarriers. Solid carriers are mineral earths, such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers, such asammonium sulfate, ammonium phosphate, ammonium nitrate, ureas andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powder, or other solid carriers.

The concentrations of the active ingredients I in the ready-to-usepreparations can be varied within wide limits. In general, theformulations comprise from 0.001 to 98% by weight, preferably 0.01 to95% by weight, of at least one active ingredient. The active ingredientsare employed in a purity of from 90% to 100%, preferably 95% to 100% (inaccordance with NMR spectrum).

The formulation examples which follow illustrate the preparation of suchproducts:

I. 20 parts by weight of compound No. It.10 are dissolved in a mixturecomposed of 80 parts by weight of alkylated benzene, 10 parts by weightof the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acidN-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonateand 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 molof castor oil. Pouring the solution into 100,000 parts by weight ofwater and finely distributing it therein leaves an aqueous dispersioncomprising 0.02% by weight of the active ingredient.

II. 20 parts by weight of compound No. 1.02 are dissolved in a mixturecomposed of 40 parts by weight of cyclohexanone, 30 parts by weight ofisobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxideto 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into100,000 parts by weight of water and finely distributing it thereingives an aqueous dispersion comprising 0.02% by weight of the activeingredient.

III. 20 parts by weight of active ingredient No. 1.03 are dissolved in amixture composed of 25 parts by weight of cyclohexanone, 65 parts byweight of a mineral oil fraction of boiling point 210 to 280° C. and 10parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol ofcastor oil. Pouring the solution into 100,000 parts by weight of waterand finely distributing it therein gives an aqueous dispersioncomprising 0.02% by weight of the active ingredient.

IV. 20 parts by weight of active ingredient No. 1.05 are mixedthoroughly with 3 parts by weight of sodiumdiisobutylnaphthalene-α-sulfonate, 17 parts by weight of the sodium saltof a lignosulfonic acid from a sulfite waste liquor and 60 parts byweight of pulverulent silica gel, and the mixture is ground in a hammermill. Finely distributing the mixture in 20,000 parts by weight of watergives a spray mixture comprising 0.1% by weight of the activeingredient.

V. 3 parts by weight of active ingredient No. 1.04 are mixed with 97parts by weight of finely divided kaolin. This gives a dust comprising3% by weight of the active ingredient.

VI. 20 parts by weight of active ingredient No. 1.16 are mixedintimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8parts by weight of fatty alcohol polyglycol ether, 2 parts by weight ofthe sodium salt of a phenol/urea/formaldehyde condensate and 68 parts byweight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of active ingredient No. 1.17 is dissolved in amixture composed of 70 parts by weight of cyclohexanone, 20 parts byweight of ethoxylated isooctylphenol and 10 parts by weight ofethoxylated castor oil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of active ingredient No. 1.18 is dissolved in amixture composed of 80 parts by weight of cyclohexanone and 20 parts byweight of Uniperol® EL (=non-ionic emulsifier based on ethoxylatedcastor oil). This gives a stable emulsion concentrate.

The active ingredients I or the herbicidal compositions comprising themcan be applied pre- or post-emergence. If the active ingredients areless well tolerated by certain crop plants, application techniques maybe used where the herbicidal compositions are sprayed, with the aid ofthe spraying apparatus, in such a manner that the active ingredientscome into as little contact as possible with the leaves of the sensitivecrop plants while reaching the leaves of undesirable plants which growthereunder, or the naked soil surface (post-directed, lay-by).

Depending on the intended control target, the season, the target plantsand the growth stage, the application rates of active ingredient I arefrom 0.001 to 3.0, preferably 0.01 to 1.0, kg of active ingredient(a.i.) per ha.

To widen the spectrum of action and to achieve synergistic effects, thebenzylhydroxylamines I may be mixed with a large number ofrepresentatives of other groups of herbicidal or growth-regulatingactive ingredients and then applied concomitantly. Suitable componentsfor mixtures are for example 1,2,4-thiadiazoles, 1,3,4-thiadiazoles,amides, aminophosphoric acid and its derivatives, aminotriazoles,anilides, aryloxy/hetaryloxyalkanoic acids and their derivatives,benzoic acid and its derivatives, benzothiadiazinones,2-(hetaroyl/aroyl)-1,3-cyclohexanediones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃ -phenyl derivatives, carbamates,quinolinecarboxylic acid and its derivatives, chloroacetanilides,cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid andits derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionicesters, phenylacetic acid and its derivatives, 2-phenylpropionic acidand its derivatives, pyrazoles, phenylpyrazoles, pyridazines,pyridinecarboxylic acid and its derivatives, pyrimidyl ethers,sulfonamides, sulfonylureas, triazines, triazinones, triazolinones,triazolecarboxamides and uracils.

Furthermore, it may be advantageous to apply the compounds I, alone orin combination with other herbicides, together with other cropprotection agents, for example with pesticides or agents for controllingphytopathogenic fungi or bacteria. Also of interest is the miscibilitywith mineral salt solutions, which are employed for treating nutrientand trace element deficiencies. Non-phytotoxic oils and oil concentratesmay also be added.

PREPARATION EXAMPLES Example 13-(4-Chloro-3-methoxyaminomethylphenyl)-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione(compound No. 1.01)

Triethylsilane (1.9 ml) was added dropwise to a solution of3-(4-chloro-3-methoxyiminomethylphenyl)-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione(3.6 g) in a mixture of 30 ml of dichloromethane and 50 ml oftrifluoroacetic acid. After the mixture had been stirred for 20 hours atroom temperature, the solvent was distilled off. The residue was takenup in 200 ml of dichloromethane, whereupon the organic phase was washedfour times using 50 ml of water in each case, dried over sodium sulfateand finally concentrated. Crystallization using diisopropyl ether andpetroleum ether gave the title compound (m.p. 83-85° C.).

Example 23-(4-Chloro-3-ethoxyaminomethylphenyl)-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione(compound No. 1.02)

Borane-pyridine complex (3 ml) and 10-percent hydrochloric acid (30 ml)were added dropwise in succession at 0° C. to a solution of3-(4-chloro-3-ethoxyiminomethylphenyl)-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione(3.8 g) in 40 ml of ethanol. In the course of 16 hours, another 12 ml ofboranepyridine complex were added. The solution was subsequently stirredfor 4 hours at reflux temperature, whereupon the solvent was distilledoff. The residue was taken up in 200 ml of dichloromethane. The organicphase was washed twice using 50 ml of water in each case, then driedover sodium sulfate, and finally concentrated. This gave the titlecompound as an oil.

Example 33-(3-[Acetyl(methoxyamino)methyl]-4-chlorophenyl)-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione(compound No. 1.04)

3-(4-Chloro-3-methoxyaminomethylphenyl)-1-methyl-6-trifluoroethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione(1.6 g in 30 ml of tetrahydrofuran) was added dropwise to a suspensionof sodium hydride (0.17 g in 50 ml of tetrahydrofuan [sic]). After onehour, acetyl chloride (0.4 g in 20 ml of tetrahydrofuran) was added. Themixture was stirred for 20 hours at room temperature and subsequentlytreated with water (100 ml). The desired product was extracted from theaqueous phase by using 2×100 ml of dichloromethane. The combined organicphases were washed three times using water, dried over sodium sulfateand freed from the solvent. Silica gel chromatography (eluent:dichloromethane/ethyl acetate 9:1) and crystallization using petroleumether gave the title compound (m.p. 160-161° C.).

Example 43-(3-[(Methoxymethylamino)methyl]-4-chlorophenyl)-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione(compound No. 1.06)

3-(3-Bromomethyl)-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione(0.005 mol) were added to a mixture of methoxyethylamine (0.06 mol),potassium carbonate (0.012 mol) and 100 ml of dimethylformamide. After 5hours at room temperature, the reaction solution was concentrated. Theresidue was treated with 100 ml of methylene chloride, whereupon theorganic phase was washed 3 times using 30 ml of water in each case, thendried over sodium sulfate and finally concentrated. The desired valuableproduct was obtained from the resulting oil by adding petroleum ether.

Example 53-(3-[Ethoxycarbonylaminooxymethyl]-4-chloro-6-fluorophenyl)-1-amino-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione(Compound No. It.10)

0.9 g of carbonyldiimidazole was added to a solution of 1.8 g of3-(3-hydroxymethyl-4-chloro-6-fluorophenyl)-1-amino-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dionein 100 ml of tetrahydrofuran. After the reaction mixture had beenstirred for 1 hour, 0.58 g of N-ethoxycarbonylhydroxylamine was added.The mixture was subsequently stirred for a further 14 hours at 20° C.whereupon the solvent was removed by distillation. The residue was takenup in 100 ml of methylene chloride. The resulting organic phase waswashed with water, dried over sodium sulfate and finally concentrated.The crude product was purified by means of chromatography on silica gel(eluent: methylene chloride). Yield: 0.2 g.

In addition to the compounds described above, other benzylhydroxylaminesI which were, or can be, prepared by a similar method are listed inTable 4 below:

                                      TABLE 4                                     __________________________________________________________________________                                         I                                                                               #STR46##                                  -                                                                                                            m.p.                                          No.   Y   R1.sup.  R.sup.2 R.sup.3    R.sup.4  R.sup.5 R.sup.6 R.sup.7                                                  R.sup.8 [° C.]             __________________________________________________________________________    1.01                                                                             O  Cl                                                                              H  CH.sub.3                                                                         CF.sub.3                                                                          H H  H       CH.sub.3                                                                         83-85                                         1.02  O   Cl  H  CH.sub.3   CF.sub.3 H  H  H             C.sub.2                                              H.sub.5    oil                                1.03  O   Cl  H  CH.sub.3   CF.sub.3 H  H  COOC.sub.2 H.sub.5 CH.sub.3                                             oil                                      1.04  O   Cl  H  CH.sub.3   CF.sub.3 H  H  COCH.sub.3      CH.sub.3                                                 160-161                                 1.05  O   Cl  F  NH.sub.2   CF.sub.3 H  H  H             CH.sub.3                                                  63-67                                    1.06  O   Cl  H  CH.sub.3   CF.sub.3 H  H  CH.sub.3       CH.sub.3                                             1.07  O   Cl  F  NH.sub.2   CF.sub.3 H                                        H  CH.sub.3       H            153-155       1.08  O   Cl  F  NH.sub.2   CF.sub.3 H  H  COOCH.sub.3    CH.sub.3                                                112-115                                   1.09  O   Cl  F  NH.sub.2   CF.sub.3 H  H  COCH.sub.3     CH.sub.3                                                  119-121                                 1.10  O   Cl  F  NH.sub.2   CF.sub.3 H  H  COCHCl.sub.2   CH.sub.3                                                122-125                                   1.11  O   Cl  F  NH.sub.2   CF.sub.3 H  H  CO-cyclopropyl CH.sub.3                                                 85-89                                    1.12  O   Cl  F  NH.sub.2   CF.sub.3 H  H  CH.sub.3        CH.sub.3                                                oil                                      1.13  O   CI  F  NH.sub.2   CF.sub.3 H  H  COCH.sub.2 OCOCH.sub.3                                             CH.sub.3     90-94                            1.14  O   Cl  F  NH.sub.2   CF.sub.3 H  H  COSCH.sub.3     CH.sub.3                                                 113-120                                 1.15  O   Cl  F  NH.sub.2   CF.sub.3 H  H  COC.sub.2 H.sub.5 CH.sub.3                                              133-136                                  1.16  O   Cl  F  NH.sub.2   CF.sub.3 H  H  COOC.sub.2 H.sub.5 CH.sub.3                                             115-117                                  1.17  O   Cl  F  NH.sub.2   CF.sub.3 H  H  COCF.sub.3      CH.sub.3                                                 162-164                                 1.18  O   Cl  F  NH.sub.2   CF.sub.3 H  H  CONH--C.sub.6 H.sub.5                                              CH.sub.3     138-143                        __________________________________________________________________________

USE EXAMPLES (Herbicidal Activity)

The herbicidal action of the benzylhydroxylamines I was demonstrated bythe following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as substrate. The seeds for thetest plants were sown separately for each species.

In the case of the pre-emergence treatment, the active ingredients,which were suspended or emulsified in water, were applied directly aftersowing by means of finely distributing nozzles. The containers wereirrigated gently to promote germination and growth and subsequentlycovered with translucent plastic hoods until the plants had rooted. Thiscover results in uniform germination of the test plants, unlessgermination was adversely affected by the active ingredients.

For the post-emergence treatment, the test plants were first grown to aplant height of 3 to 15 cm, depending on the growth form, and only thentreated with the active ingredients which were suspended or emulsifiedin water. The test plants were either sown directly and grown in thesame containers, or were first grown separately as seedlings andtransplanted to the test containers a few days prior to treatment. Therate of the application for the post-emergence treatment was 0.0156,0.0078, 0.0039 or 0.0019 kg of a.i. (active ingredient) per ha.

The plants were kept at from 10 to 25° C. or 20 to 35° C., depending onthe species. The test period extended to 2 to 4 weeks. During this time,the plants were tended, and their response to the individual treatmentswas evaluated.

The plants were scored using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialparts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments were of the followingspecies:

    ______________________________________                                        Scientific Name     English Name                                              ______________________________________                                        Abutilon theophrasti                                                                              Velvet leaf                                                 Galium aparine Catchweed bedstraw                                             Sinapis alba White mustard                                                    Solanum nigrum Black nightshade                                               Veronica subspecies Speedwell                                               ______________________________________                                    

At a rate of application of 0.0156 or 0.0078 kg of a.i./ha, compound No.1.03 was very effective against Abutilon theophrasti, Solanum nigrum andvarious Veronica species when used post-emergence.

At a rate of application of 3.9 or 1.9 g of a.i./ha, compound No. It.10was very effective against Galium aparine, Sinapis alba and Solanumnigrum when used post-emergence.

USE EXAMPLES (Desiccant/defoliant Activity)

The test plants used were young cotton plants with 4 leaves (withoutcotyledons), which had been grown under greenhouse conditions (relativeatmospheric humidity 50 to 70%; day/night temperature=27/20° C.).

The young cotton plants were given foliar treatments to runoff pointusing the aqueous preparations of the active ingredients (with anaddition of 0.15% by weight of the fatty alcohol alkoxylate Plurafac LF700, based on the spray mixture). The amount of water applied was 10001/ha (converted). After 13 days, the number of shed leaves and thedegree of defoliation in % were determined.

No leaves were shed by the untreated control plants.

We claim:
 1. A benzylhydroxylamine of the formula I ##STR47## in whichthe variables have the following meanings: X is --N(R⁷)--O-- which canbe bonded to R⁸ via oxygen or nitrogen;Y is oxygen or sulfur; R¹ ishalogen, cyano, nitro or trifluoromethyl; R² is hydrogen or halogen; R³is hydrogen, amino or methyl; R⁴ is hydrogen, halogen, C₁ -C₆ -alkyl, C₁-C₆ -haloalkyl, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl or C₁ -C₆-alkylsulfonyl; R⁵ is hydrogen, halogen or C₁ -C₆ -alkyl; R⁶ ishydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -cycloalkyl or C₂ -C₆-alkenyl; R⁷ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₈ -cycloalkyl, C₁ -C₆-haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, (C₁ -C₆ -alkyl)carbonyl,(C₃ -C₆ -alkenyl)carbonyl, (C₃ -C₆ -alkynyl)carbonyl, (C₁ -C₆-alkoxy)carbonyl, (C₂ -C₆ -alkenyloxy) carbonyl, (C₂ -C₆ -alkynyloxy)carbonyl, (C₁ -C₆ -alkylthio)carbonyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylcarbamoyl, where each of the last mentioned 14 radicals isunsubstituted or carries one to three substituents selected from thegroup consisting ofnitro, cyano, halogen, C₃ -C₈ -cycloalkyl, hydroxyl,C₁ -C₆ -alkoxy, C₃ -C₈ cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆-alkynyloxy, C₁ -C₆ -alkoxy-C₃ -C₆ -alkoxy, C₁ -C₆ -alkylthio, (C₁ -C₆-alkyl)carbonyl, (C₁ -C₆ -alkyl) carbonyloxy, C₁ -C₆ -alkylsulfinyl, C₁-C₆ -alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy, C₁ -C₆ -alkylcarbamoyl,phenyl, phenoxy or phenylsulfonyl, where the phenyl rings areunsubstituted or carry one to three substituents selected from the groupconsisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy andC₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl or heterocyclyloxygroup having one to three hetero atoms, selected from the groupconsisting of two oxygen atoms, two sulfur atoms and 3 nitrogen atoms,where the heterocycle is saturated, partially or fully unsaturated oraromatic, and, where the heterocycle is unsubstituted or carries one tothree substituents selected from the group consisting of halogen, nitro,cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyl and (C₁ -C₆-alkyl)carbonyl, a group --CO--Z¹ R⁹, --OCO--Z¹ R⁹ or --N(R⁹)R¹⁰, or R⁷is C₃ -C₈ -cycloalkylcarbonyl, phenylcarbonyl, phenylsulfonyl orphenylcarbamoyl, where these 4 radicals are unsubstituted or carry oneto three substituents selected from the group consisting of halogen,nitro, cyano, C₃ -C₆ -alkyl, C₁ -C₆ -alkoxy and C₁ -C₆ -haloalkyl; R⁸ ishydrogen, C₁ -C₆ -alkyl, C₃ -C₈ -cycloalkyl, C₁ -C₆ -haloalkyl, C₃ -C₆-alkenyl or C₃ -C₆ -alkynyl, where each of the last-mentioned 5 radicalsis unsubstituted or carries one to three substituents selected from thegroup consisting ofnitro, cyano, halogen, C₃ -C₈ -cycloalkyl, hydroxyl,C₁ -C₆ -alkoxy, C₃ -C₈ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆-alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆-alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy,phenyl, phenoxy or phenylsulfonyl, where the phenyl rings areunsubstituted or carry one to three substituents selected from the groupconsisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy andC₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl or heterocyclyloxygroup having one to three hetero atoms, selected from the groupconsisting of two oxygen atoms, two sulfur atoms and 3 nitrogen atoms,where the heterocycle is saturated, partially or fully unsaturated oraromatic, and, where the heterocycle is unsubstituted or carries one tothree substituents selected from the group consisting of halogen, nitro,cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyl and (C₁ -C₆-alkyl)carbonyl, a group --CO--Z² R¹¹, --OCO--Z² R¹¹ or --N(R¹¹)R¹² ; Z¹is a chemical bond, oxygen, sulfur or --N(R¹⁰)--; Z² is a chemical bond,oxygen, sulfur or --N(R¹²)--; R⁹, R¹¹ independently of one another arehydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₈ -cycloalkyl, C₃ -C₆-alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, (C₁ -C₆-alkoxy)carbonyl-C₁ -C₆ -alkyl, phenyl or phenyl-C₁ -C₆ -alkyl, wherethe phenyl and the phenyl ring of the phenylalkyl group is unsubstitutedor carries one to three radicals selected from the group consisting ofnitro, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxyor (C₁ -C₆ -alkyl)carbonyl, or Z¹ and R⁹ and/or Z² and R¹¹ in each casetogether are a 3- to 7-membered heterocycle bonded via nitrogen andhaving one to three hetero atoms selected from the group consisting oftwo oxygen atoms, two sulfur atoms and 3 nitrogen atoms, where theheterocycle is saturated, partially or fully unsaturated or aromatic andwhere the heterocycle is unsubstituted or carries one to threesubstituents selected from the group consisting of nitro, cyano,halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl and C₁ -C₆ -alkoxy; R¹⁰, R¹²independently of one another are hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₃-C₈ -cycloalkyl or C₁ -C₆ -alkoxy,or an agriculturally useful salt of acompound I where R³, R⁷ and/or R⁸ is hydrogen.
 2. A benzylhydroxylamineof the formula I as claimed in claim 1, where the variables have thefollowing meanings:Y is oxygen; R¹ is halogen or cyano; R² is hydrogen,fluorine or chlorine; R³ is amino or methyl; R⁴ is C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl or C₁ -C₆ -alkylsulfonyl; R⁵ is hydrogen or halogen; R⁶ ishydrogen or C₁ -C₄ -alkyl; R⁷ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₈-cycloalkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, (C₁-C₆ -alkyl)carbonyl, (C₃ -C₆ -alkenyl)carbonyl, (C₃ -C₆-alkynyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, (C₂ -C₆ -alkenyloxy)carbonyl, (C₂ -C₆ -alkynyloxy)carbonyl, (C₁ -C₆ -alkylthio)carbonyl, C₁-C₆ -alkylcarbamoyl, where each of the last mentioned 13 radicals isunsubstituted or carries one or two substituents selected from the groupconsisting ofnitro, cyano, halogen, C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆-alkoxy, C₃ -C₈ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁-C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl, C₁-C₆ -alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy, and a group --CO--Z¹ R⁹,--OCO--Z¹ R⁹ or --N(R⁹)R¹⁰, R⁸ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₈-cycloalkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl or C₃ -C₆ -alkynyl,where each of the last-mentioned 5 radicals is unsubstituted or carriesone or two substituents selected from the group consisting ofnitro,cyano, halogen, C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈-cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁-C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy, and a group --CO--Z² R¹¹,--OCO--Z² R¹¹ or --N(R¹¹)R¹² ; Z¹ is a chemical bond, oxygen, sulfur or--N(R¹⁰)--; Z² is a chemical bond, oxygen, sulfur or --N(R¹²)--; R⁹, R¹¹independently of one another are hydrogen, C₁ -C₆ -alkyl, C₃ -C₈-cycloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl or (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl, or Z¹ and R⁹ and/or Z²and R¹¹ in each case together are a 3- to 7-membered heterocycle bondedvia nitrogen and having one to three hetero atoms selected from thegroup consisting of two oxygen atoms, two sulfur atoms and 3 nitrogenatoms, where the heterocycle is saturated, partially or fullyunsaturated or aromatic and where the heterocycle is unsubstituted orcarries one to three substituents selected from the group consisting ofnitro, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl and C₁ -C₆-alkoxy; R¹⁰, R¹² independently of one another are hydrogen or C₁ -C₆-alkyl.
 3. A herbicidal composition comprising a herbicidally activeamount of at least one benzylhydroxylamine of the formula I or at leastone agriculturally useful salt of I as defined in claim 1 and at leastone inert liquid or solid carrier and optionally at least onesurfactant.
 4. A composition for the desiccation and/or defoliation ofplants, comprising an amount of at least one benzylhydroxylamine of theformula I or at least one agriculturally useful salt of I as defined inclaim 1 which has a desiccant or defoliant action and at least one inertliquid or solid carrier and optionally at least one surfactant.
 5. Aprocess for the preparation of herbicidally active compositions, whichcomprises mixing a herbicidally active amount of at least onebenzylhydroxylamine of the formula I or at least one agriculturallyuseful salt of I as defined in claim 1 and at least one inert liquid orsolid carrier and optionally at least one surfactant.
 6. A process forthe preparation of a composition having a desiccant and/or defoliantaction, which comprises mixing an amount of at least onebenzylhydroxylamine of the formula I or at least one agriculturallyuseful salt of I as defined in claim 1 which has a desiccant ordefoliant action and at least one inert liquid or solid carrier andoptionally at least one surfactant.
 7. A method of controllingundesirable vegetation, which comprises allowing a herbicidally activeamount of at least one benzylhydroxylamine of the formula I or at leastone agriculturally useful salt of I as defined in claim 1 to act onplants, their environment or on seed.
 8. A method for the desiccationand/or defoliation of plants, which comprises allowing an amount of atleast one benzylhydroxylamine of the formula I or at least oneagriculturally useful salt of I as defined in claim 1 which has adesiccant or defoliant action to act on plants.
 9. An enamine ester ofthe formula IV ##STR48## where L¹ is C₁ -C₆ -alkyl or phenyl andX is--N(R⁷)--O-- which can be bonded to R⁸ via oxygen or nitrogen; Y isoxygen or sulfur: R¹ is halogen, cyano, nitro or trifluoromethyl; R² ishydrogen or halogen; R³ is hydrogen, amino or methyl; R⁴ is hydrogen,halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylthio, C₁ -C₆-alkylsulfinyl or C₁ -C₆ -alkylsulfonyl; R⁵ is hydrogen, halogen or C₁-C₅ -alkyl; R⁶ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆-cycloalkyl or C₁ -C₆ -alkenyl; R⁷ is hydrogen, C₁ -C₆ -alkyl, C₃ C₈-cycloalkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, (C₁-C₆ -alkyl)carbonyl, (C₃ -C₆ -alkenyl)carbonyl, (C₃ -C₆-alkynyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, (C₂ -C₆-alkenyloxy)carbonyl, (C₂ -C₆ -alkynyloxy)carbonyl, (C₁ -C₆-alkylthio)carbonyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylcarbamoyl,where each of the last mentioned 14 radicals is unsubstituted or carriesone to three substituents selected from the group consisting ofnitro,cyano, halogen, C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁-C₆ -alkoxy, C₁ -C₆ -alkylthio, (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆-alkyl)carbonyloxy, C₁ -C₆ -alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylideneaminoxy, C₁ -C₆ -alkylcarbamoyl, phenyl, phenoxy orphenylsulfonyl, where the phenyl rings are unsubstituted or carry one tothree substituents selected from the group consisting of halogen, nitro,cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy and C₁ -C₆ -haloalkyl, a 3- to7-membered heterocyclyl or heterocyclyloxy group having one to threehetero atoms, selected from the group consisting of two oxygen atoms,two sulfur atoms and 3 nitrogen atoms, where the heterocycle issaturated, partially or fully unsaturated or aromatic, and, where theheterocycle is unsubstituted or carries one to three substituentsselected from the group consisting of halogen, nitro, cyano, C₁ -C₆-alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyl and (C₁ -C₆ -alkyl) carbonyl,a group --CO--Z¹ R⁹, --OCO--Z¹ R⁹ or --N(R⁹)R¹⁰, or R⁷ is C₃ -C₈-cycloalkylcarbonyl, phenylcarbonyl, phenylsulfonyl or phenylcarbamoyl,where these 4 radicals are unsubstituted or carry one to threesubstituents selected from the group consisting of halogen, nitro,cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy and C₁ -C₆ -haloalkyl; R⁸ ishydrogen, C₁ -C₆ -alkyl, C₃ -C₈ -cycloalkyl, C₁ -C₆ -haloalkyl, C₃ -C₆-alkenyl or C₃ -C₆ -alkynyl, where each of the last-mentioned 5 radicalsis unsubstituted or carries one to three substituents selected from thegroup consisting ofnitro, cyano, halogen, C₃ -C₈ -cycloalkyl, hydroxyl,C₁ -C₆ -alkoxy, C₃ -C₈ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆-alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆-alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy,phenyl, phenoxy or phenylsulfonyl, where the phenyl rings areunsubstituted or carry one to three substituents selected from the groupconsisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy andC₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl or heterocyclyloxygroup having one to three hetero atoms, selected from the groupconsisting of two oxygen atoms, two sulfur atoms and 3 nitrogen atoms,where the heterocycle is saturated, partially or fully unsaturated oraromatic, and, where the heterocycle is unsubstituted or carries one tothree substituents selected from the group consisting of halogen, nitro,cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyl and (C₁ -C₆-alkyl)carbonyl, a group --CO--Z² R¹¹, --OCO--Z² R¹¹ or --N(R¹¹)R¹² ; Z¹is a chemical bond, oxygen, sulfur or --N(R¹⁰)--; Z² is a chemical bond,oxygen, sulfur or --N(R¹²)--; R⁹, R¹¹ independently of one another arehydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₈ -cycloalkyl, C₃ -C₆-alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, (C₁ -C₆-alkoxy)carbonyl-C₁ -C₆ -alkyl, phenyl or phenyl-C₁ -C₆ -alkyl, wherethe phenyl and the phenyl ring of the phenylalkyl group is unsubstitutedor carries one to three radicals selected from the group consisting ofnitro, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxyor (C₁ -C₆ -alkyl)carbonyl, or Z¹ and R⁹ and/or Z² and R¹¹ in each casetogether are a 3- to 7-membered heterocycle bonded via nitrogen andhaving one to three hetero atoms selected from the group consisting oftwo oxygen atoms, two sulfur atoms and 3 nitrogen atoms, where theheterocycle is saturated, partially or fully unsaturated or aromatic andwhere the heterocycle is unsubstituted or carries one to threesubstituents selected from the group consisting of nitro, cyano,halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl and C₁ -C₆ -alkoxy; R¹⁰, R¹²independently of one another are hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₃-C₈ -cycloalkyl or C₁ -C₆ -alkoxy.
 10. An enamine carboxylate of theformula V ##STR49## where L¹ is C₁ -C₆ -alkyl or phenyl and X is--N(R⁷)--O-- which can be bonded to R⁸ via oxygen or nitrogen;Y isoxygen or sulfur; R¹ is halogen, cyano, nitro or trifluoromethyl; R² ishydrogen or halogen; R³ is hydrogen, amino or methyl; R⁴ is hydrogen,halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylthio, C₁ -C₆-alkylsulfinyl or C₁ -C₆ -alkylsulfonyl; R⁵ is hydrogen, halogen or C₁-C₆ -alkyl; R⁶ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆-cycloalkyl or C₂ -C₆ -alkenyl; R⁷ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₈-cycloalkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, (C₁-C₆ -alkyl carbonyl, (C₃ -C₆ -alkenyl)carbonyl, (C₃ -C₆-alkynyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, (C₂ -C₆-alkenyloxy)carbonyl, C₂ -C₆ -alkynyloxy)carbonyl, (C₁ -C₆ -alkylthio)carbonyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylcarbamoyl, where each ofthe last mentioned 14 radicals is unsubstituted or carries one to threesubstituents selected from the group consisting ofnitro, cyano, halogen,C₃ -C₈ -cycloalkyl hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈ cycloalkoxy, C₃ -C₆-alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆-alkylthio, (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -alkyl) carbonyloxy, C₁ -C₆-alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy, C₁ -C₆-alkylcarbamoyl, phenyl, phenoxy or phenylsulfonyl, where the phenylrings are unsubstituted or carry one to three substituents selected fromthe group consisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy and C₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl orheterocyclyloxy group having one to three hetero atoms, selected fromthe group consisting of two oxygen atoms, two sulfur atoms and 3nitrogen atoms, where the heterocycle is saturated, partially or fullyunsaturated or aromatic, and, where the heterocycle is unsubstituted orcarries one to three substituents selected from the group consisting ofhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₅ -haloalkyland (C₁ -C₆ -alkyl) carbonyl, a group --CO--Z¹ R⁹, --OCO--Z¹ R⁹ or--N(R⁹)R¹⁰, or R⁷ is C₃ -C₈ -cycloalkylcarbonyl, phenylcarbonyl,phenylsulfonyl or phenylcarbamoyl, where these 4 radicals areunsubstituted or carry one to three substituents selected from the groupconsisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy andC₁ -C₆ -haloalkyl; R⁸ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -cycloalkyl, C₁-C₆ -haloalkyl, C₃ -C₆ -alkenyl or C₃ -C₆ -alkynyl, where each of thelast-mentioned 5 radicals is unsubstituted or carries one to threesubstituents selected from the group consisting ofnitro, cyano, halogen,C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈ -cycloalkoxy, C₃-C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁-C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylideneaminoxy, phenyl, phenoxy or phenylsulfonyl, where the phenylrings are unsubstituted or carry one to three substituents selected fromthe group consisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy and C₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl orheterocyclyloxy group having one to three hetero atoms, selected fromthe group consisting of two oxygen atoms, two sulfur atoms and 3nitrogen atoms, where the heterocycle is saturated, partially or fullyunsaturated or aromatic, and, where the heterocycle is unsubstituted orcarries one to three substituents selected from the group consisting ofhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyland (C₁ -C₆ -alkyl)carbonyl, a group --CO--Z² R¹¹, --OCO--Z² R¹¹ or--N(R¹¹)R¹² ; Z¹ is a chemical bond, oxygen, sulfur or --N(R¹⁰)--; Z² isa chemical bond, oxygen, sulfur or --N(R¹²)--; R⁹, R¹¹ independently ofone another are hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₈-cycloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl, phenyl or phenyl-C₁ -C₆-alkyl, where the phenyl and the phenyl ring of the phenylalkyl group isunsubstituted or carries one to three radicals selected from the groupconsisting of nitro, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₁ -C₆ -alkoxy or (C₁ -C₆ -alkyl)carbonyl, or Z¹ and R⁹ and/or Z² andR¹¹ in each case together are a 3- to 7-membered heterocycle bonded vianitrogen and having one to three hetero atoms selected from the groupconsisting of two oxygen atoms, two sulfur atoms and 3 nitrogen atoms,where the heterocycle is saturated, partially or fully unsaturated oraromatic and where the heterocycle is unsubstituted or carries one tothree substituents selected from the group consisting of nitro, cyano,halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl and C₁ -C₆ -alkoxy; R¹⁰, R¹²independently of one another are hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₃-C₈ -cycloalkyl or C₁ -C₆ -alkoxy.
 11. A phenylurea derivative of theformula XIII ##STR50## where X is --N(R⁷)--O-- which can be bonded to R⁸via oxygen or nitrogen;R¹ is halogen, cyano, nitro or trifluoromethyl;R² is hydrogen or halogen; R³ is hydrogen, amino or methyl; R⁶ ishydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -cycloalkyl or C₂ -C₆-alkenyl; R⁷ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -cycloalkyl, C₁ -C₆-haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, (C₁ -C₆ -alkyl)carbonyl,(C₃ -C₆ -alkenyl)carbonyl, (C₃ -C₆ -alkynyl)carbonyl, (C₁ -C₆-alkoxy)carbonyl, (C₁ -C₆ -alkenyloxy) carbonyl, (C₂ -C₆-alkynyloxy)carbonyl, (C₁ -C₆ -alkylthio) carbonyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylcarbamoyl, where each of the last mentioned14 radicals is unsubstituted or carries one to three substituentsselected from the group consisting ofnitro, cyano, halogen, C₃ -C₈-cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈ cycloalkoxy, C₃ -C₆-alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆-alkylthio, (C₁ -C₆ -alkyl) carbonyl, (C₁ -C₆ -alkyl) carbonyloxy, C₁-C₆ -alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy, C₁-C₆ -alkylcarbamoyl, phenyl, phenoxy or phenylsulfonyl, where the phenylrings are unsubstituted or carry one to three substituents selected fromthe group consisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy and C₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl orheterocyclyloxy group having one to three hetero atoms, selected fromthe group consisting of two oxygen atoms, two sulfur atoms and 3nitrogen atoms, where the heterocycle is saturated, partially or fullyunsaturated or aromatic, and, where the heterocycle is unsubstituted orcarries one to three substituents selected from the group consisting ofhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyland (C₁ -C₆ -alkyl)carbonyl, a group --CO--Z¹ R⁹, --OCO--Z¹ R⁹ or--N(R⁹)R¹⁰, or R⁷ is C₃ -C₈ -cycloalkylcarbonyl, phenylcarbonyl,phenylsulfonyl or phenylcarbamoyl, where these 4 radicals areunsubstituted or carry one to three substituents selected from the groupconsisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy andC₁ -C₆ -haloalkyl; R⁸ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₈ -cycloalkyl, C₁-C₆ -haloalkyl, C₃ -C₆ -alkenyl or C₃ -C₆ -alkynyl, where each of thelast-mentioned 5 radicals is unsubstituted or carries one to threesubstituents selected from the group consisting ofnitro, cyano, halogen,C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈ -cycloalkoxy, C₃-C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁-C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylideneaminoxy, phenyl, phenoxy or phenylsulfonyl, where the phenylrings are unsubstituted or carry one to three substituents selected fromthe group consisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy and C₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl orheterocyclyloxy group having one to three hetero atoms, selected fromthe group consisting of two oxygen atoms, two sulfur atoms and 3nitrogen atoms, where the heterocycle is saturated, partially or fullyunsaturated or aromatic, and, where the heterocycle is unsubstituted orcarries one to three substituents selected from the group consisting ofhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyland C₁ -C₆ -alkyl) carbonyl, a group --CO--Z² R¹¹, --OCO--Z² R¹¹ or--N(R¹¹)R¹² ; Z¹ is a chemical bond, oxygen, sulfur or --N(R¹⁰)--; Z² isa chemical bond, oxygen, sulfur or --N(R¹²)--; R⁹, R¹¹ independently ofone another are hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₈-cycloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl, (C₁ -C₆ -alkoxy )carbonyl-C₁ -C₆ -alkyl, phenyl or phenyl-C₁ -C₆-alkyl, where the phenyl and the phenyl ring of the phenylalkyl group isunsubstituted or carries one to three radicals selected from the groupconsisting of nitro, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₁ -C₆ -alkoxy or (C₁ -C₆ -alkyl)carbonyl, or Z¹ and R⁹ and/or Z² andR¹¹ in each case together are a 3- to 7-membered heterocycle bonded vianitrogen and having one to three hetero atoms selected from the groupconsisting of two oxygen atoms, two sulfur atoms and 3 nitrogen atoms,where the heterocycle is saturated, partially or fully unsaturated oraromatic and where the heterocycle is unsubstituted or carries one tothree substituents selected from the group consisting of nitro, cyano,halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl and C₁ -C₆ -alkoxy; R¹⁰, R¹²independently of one another are hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₃-C₈ -cycloalkyl or C₁ -C₆ -alkoxy.
 12. A phenylisocyanate of the formulaXVI ##STR51## where X is --N(R⁷)--O-- which can be bonded to R⁸ viaoxygen or nitrogen;R¹ is halogen, cyano, nitro or trifluoromethyl; R² ishydrogen or halogen; R⁶ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₃ -C₆ -cycloalkyl or C₂ -C₆ -alkenyl; R⁷ is hydrogen, C₁ -C₆ -alkyl, C₃-C₈ -cycloalkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl,(C₁ -C₆ -alkyl carbonyl, (C₃ -C₆ -alkenyl)carbonyl, (C₃ -C₆ -alkynylcarbonyl, (C₁ -C₆ -alkoxy)carbonyl, (C₂ -C₆ -alkenyloxy)carbonyl, (C₂-C₆ -alkynyloxy carbonyl, (C₁ -C₆ -alkylthio)carbonyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylcarbamoyl, where each of the last mentioned14 radicals is unsubstituted or carries one to three substituentsselected from the group consisting ofnitro, cyano, halogen, C₃ -C₈-cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈ cycloalkoxy, C₃ -C₆-alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆-alkylthio, (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -alkyl) carbonyloxy, C₁ -C₆-alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy, C₁ -C₆-alkylcarbamoyl, phenyl, phenoxy or phenylsulfonyl, where the phenylrings are unsubstituted or carry one to three substituents selected fromthe group consisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy and C₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl orheterocyclyloxy group having one to three hetero atoms, selected fromthe group consisting of two oxygen atoms, two sulfur atoms and 3nitrogen atoms, where the heterocycle is saturated, partially or fullyunsaturated or aromatic, and, where the heterocycle is unsubstituted orcarries one to three substituents selected from the group consisting ofhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyland (C₁ -C₆ -alkyl)carbonyl, a group --CO--Z¹ R⁹, --OCO--Z¹ R⁹ or--N(R⁹)R¹⁰, or R⁷ is C₃ -C₈ -cycloalkylcarbonyl, phenylcarbonyl,phenylsulfonyl or phenylcarbamoyl, where these 4 radicals areunsubstituted or carry one to three substituents selected from the groupconsisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy andC₁ -C₆ -haloalkyl; R⁸ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₈ -cycloalkyl, C₁-C₆ -haloalkyl, C₃ -C₆ -alkenyl or C₃ -C₆ -alkynyl, where each of thelast-mentioned 5 radicals is unsubstituted or carries one to threesubstituents selected from the group consisting ofnitro, cyano, halogen,C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈ -cycloalkoxy, C₃-C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁-C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylideneaminoxy, phenyl, phenoxy or phenylsulfonyl, where the phenylrings are unsubstituted or carry one to three substituents selected fromthe group consisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy and C₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl orheterocyclyloxy group having one to three hetero atoms, selected fromthe group consisting of two oxygen atoms, two sulfur atoms and 3nitrogen atoms, where the heterocycle is saturated, partially or fullyunsaturated or aromatic, and, where the heterocycle is unsubstituted orcarries one to three substituents selected from the group consisting ofhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyland (C₁ -C₆ -alkyl) carbonyl, a group --CO--Z² R¹¹, --OCO--Z² R¹¹ or--N(R¹¹)R¹² ; Z¹ is a chemical bond, oxygen, sulfur or --N(R¹⁰)--; Z² isa chemical bond, oxygen, sulfur or --N(R¹²)--; R⁹, R¹¹ independently ofone another are hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₈-cycloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl, (C₁ -C₅ -alkoxy)carbonyl-C₁ -C₆ -alkyl, phenyl or phenyl-C₁ -C₆-alkyl, where the phenyl and the phenyl ring of the phenylalkyl group isunsubstituted or carries one to three radicals selected from the groupconsisting of nitro, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₁ -C₆ -alkoxy or (C₁ -C₆ -alkyl)carbonyl, or Z¹ and R⁹ and/or Z² andR¹¹ in each case together are a 3- to 7-membered heterocycle bonded vianitrogen and having one to three hetero atoms selected from the groupconsisting of two oxygen atoms, two sulfur atoms and 3 nitrogen atoms,where the heterocycle is saturated, partially or fully unsaturated oraromatic and where the heterocycle is unsubstituted or carries one tothree substituents selected from the group consisting of nitro, cyano,halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl and C₁ -C₆ -alkoxy; R¹⁰, R¹²independently of one another are hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₃-C₈ -cycloalkyl or C₁ -C₆ -alkoxy.
 13. An aniline derivative of theformula XVII ##STR52## where L⁴ is C₁ -C₄ -alkyl or phenyl andX is--N(R⁷)--O-- which can be bonded to R⁸ via oxygen or nitrogen; R¹ ishalogen, cyano, nitro or trifluoromethyl; R² is hydrogen or halogen; R⁶is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -cycloalkyl or C₂-C₆ -alkenyl; R⁷ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₈ -cycloalkyl, C₁ -C₆-haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, (C₁ -C₆ -alkyl)carbonyl,(C₃ -C₆ -alkenyl)carbonyl, (C₃ -C₆ -alkynyl)carbonyl, (C₁ -C₆-alkoxy)carbonyl, (C₁ -C₆ -alkenyloxy)carbonyl, (C₁ -C₆-alkynyloxy)carbonyl, (C₁ -C₆ -alkylthio) carbonyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylcarbamoyl, where each of the last mentioned14 radicals is unsubstituted or carries one to three substituentsselected from the group consisting ofnitro, cyano, halogen, C₃ -C₈-cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈ cycloalkoxy, C₃ -C₆-alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆-alkylthio, (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -alkyl) carbonyloxy, C₁ -C₆-alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy, C₁ -C₆-alkylcarbamoyl, phenyl, phenoxy or phenylsulfonyl, where the phenylrings are unsubstituted or carry one to three substituents selected fromthe group consisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy and C₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl orheterocyclyloxy group having one to three hetero atoms, selected fromthe group consisting of two oxygen atoms, two sulfur atoms and 3nitrogen atoms, where the heterocycle is saturated, partially or fullyunsaturated or aromatic, and, where the heterocycle is unsubstituted orcarries one to three substituents selected from the group consisting ofhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyland (C₁ -C₆ -alkyl) carbonyl, a group --CO--Z¹ R⁹, --OCO--Z¹ R⁹ or--N(R⁹)R¹⁰, or R⁷ is C₃ -C₈ -cycloalkylcarbonyl, phenylcarbonyl,phenylsulfonyl or phenylcarbamoyl, where these 4 radicals areunsubstituted or carry one to three substituents selected from the groupconsisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy andC₁ -C₆ -haloalkyl; R⁸ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₈ -cycloalkyl, C₁-C₆ -haloalkyl, C₃ -C₆ -alkenyl or C₃ -C₆ -alkynyl, where each of thelast-mentioned 5 radicals is unsubstituted or carries one to threesubstituents selected from the group consisting ofnitro, cyano, halogen,C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈ -cycloalkoxy, C₃-C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁-C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylideneaminoxy, phenyl, phenoxy or phenylsulfonyl, where the phenylrings are unsubstituted or carry one to three substituents selected fromthe group consisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy and C₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl orheterocyclyloxy group having one to three hetero atoms, selected fromthe group consisting of two oxygen atoms, two sulfur atoms and 3nitrogen atoms, where the heterocycle is saturated, partially or fullyunsaturated or aromatic, and, where the heterocycle is unsubstituted orcarries one to three substituents selected from the group consisting ofhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyland (C₁ -C₆ -alkyl)carbonyl, a group --CO--Z² R¹¹, --OCO--Z² R¹¹ or--N(R¹¹)R¹² ; Z¹ is a chemical bond, oxygen, sulfur or --N(R¹⁰)--; Z² isa chemical bond, oxygen, sulfur or --N(R¹²)--; R⁹, R¹¹ independently ofone another are hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₈-cycloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl, phenyl or phenyl-C₁ -C₆-alkyl, where the phenyl and the phenyl ring of the phenylalkyl group isunsubstituted or carries one to three radicals selected from the groupconsisting of nitro, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₁ -C₆ -alkoxy or (C₁ -C₆ -alkyl)carbonyl, or Z¹ and R⁹ and/or Z² andR¹¹ in each case together are a 3- to 7-membered heterocycle bonded vianitrogen and having one to three hetero atoms selected from the groupconsisting of two oxygen atoms, two sulfur atoms and 3 nitrogen atoms,where the heterocycle is saturated, partially or fully unsaturated oraromatic and where the heterocycle is unsubstituted or carries one tothree substituents selected from the group consisting of nitro, cyano,halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl and C₁ -C₆ -alkoxy; R¹⁰, R¹²independently of one another are hydrogen, hydroxyl C₁ -C₆ -alkyl, C₃-C₈ -cycloalkyl or C₁ -C₆ -alkoxy.
 14. An aniline compound of theformula XIX ##STR53## where X is --N(R⁷)--O-- which can be bonded to R⁸via oxygen or nitrogen;R¹ is halogen, cyano, nitro or trifluoromethyl;R² is hydrogen or halogen; R⁶ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₈-haloalkyl, C₁ -C₆ -cycloalkyl or C₂ -C₆ -alkenyl; R⁷ is hydrogen, C₁-C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl, C₃-C₆ -alkynyl, (C₁ -C₆ -alkyl)carbonyl, (C₃ -C₆ -alkenyl)carbonyl, (C₂-C₆ -alkynyl)carbonyl, (C₃ -C₆ -alkoxy)carbonyl, (C₂ -C₆ -alkenyloxy)carbonyl, (C₂ -C₆ -alkynyloxy)carbonyl, (C₁ -C₆ -alkylthio)carbonyl, C₁-C₆ -alkylsulfonyl, C₁ -C₆ -alkylcarbamoyl, where each of the lastmentioned 14 radicals is unsubstituted or carries one to threesubstituents selected from the group consisting ofnitro, cyano, halogen,C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈ cycloalkoxy, C₃ -C₆-alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆-alkylthio, (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -alkyl)carbonyloxy, C₁ -C₆-alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy, C₁ -C₆-alkylcarbamoyl, phenyl, phenoxy or phenylsulfonyl, where the phenylrings are unsubstituted or carry one to three substituents selected fromthe group consisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy and C₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl orheterocyclyloxy group having one to three hetero atoms, selected fromthe group consisting of two oxygen atoms, two sulfur atoms and 3nitrogen atoms, where the heterocycle is saturated, partially or fullyunsaturated or aromatic, and, where the heterocycle is unsubstituted orcarries one to three substituents selected from the group consisting ofhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyland (C₁ -C₆ -alkyl) carbonyl, a group --CO--Z¹ R⁹, --OCO--Z¹ R⁹ or--N(R⁹)R¹⁰, or R⁷ is C₁ -C⁸ -cycloalkylcarbonyl, phenylcarbonyl,phenylsulfonyl or phenylcarbamoyl, where these 4 radicals areunsubstituted or carry one to three substituents selected from the groupconsisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy andC₁ -C₆ -haloalkyl; R⁸ is hydrogen, C₃ -C₈ -cycloalkyl, C₁ -C₆-haloalkyl, C₃ -C₆ -alkenyl or C₃ -C₆ -alkynyl, where each of thelast-mentioned 4 radicals is unsubstituted or carries one to threesubstituents selected from the group consisting ofnitro, cyano, halogen,C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈ -cycloalkoxy, C₃-C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁-C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylideneaminoxy, phenyl, phenoxy or phenylsulfonyl, where the phenylrings are unsubstituted or carry one to three substituents selected fromthe group consisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy and C₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl orheterocyclyloxy group having one to three hetero atoms, selected fromthe group consisting of two oxygen atoms, two sulfur atoms and 3nitrogen atoms, where the heterocycle is saturated, partially or fullyunsaturated or aromatic, and, where the heterocycle is unsubstituted orcarries one to three substituents selected from the group consisting ofhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyland (C₁ -C₆ -alkyl) carbonyl, a group --CO--Z² R¹¹, --OCO--Z² R¹¹ or--N(R¹¹)R¹² ; Z¹ is a chemical bond, oxygen, sulfur or --N(R¹⁰)--; Z² isa chemical bond, oxygen, sulfur or --N(R¹²)--; R⁹, R¹¹ independently ofone another are hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₈-cycloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl, phenyl or phenyl-C₁ -C₆-alkyl, where the phenyl and the phenyl ring of the phenylalkyl group isunsubstituted or carries one to three radicals selected from the groupconsisting of nitro, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₁ -C₆ -alkoxy or (C₁ -C₆ -alkyl)carbonyl, or Z¹ and R⁹ and/or Z² andR¹¹ in each case together are a 3- to 7-membered heterocycle bonded vianitrogen and having one to three hetero atoms selected from the groupconsisting of two oxygen atoms, two sulfur atoms and 3 nitrogen atoms,where the heterocycle is saturated, partially or fully unsaturated oraromatic and where the heterocycle is unsubstituted or carries one tothree substituents selected from the group consisting of nitro, cyano,halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl and C₁ -C₆ -alkoxy; R¹⁰, R¹²independently of one another are hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₃-C₈ -cycloalkyl or C₁ -C₆ -alkoxy.
 15. A nitro compound of the formulaXXIII ##STR54## where X is --N(R⁷)--O-- which can be bonded to R⁸ viaoxygen or nitrogen;R¹ is halogen, cyano, nitro or trifluoromethyl; R² ishydrogen or halogen; R⁶ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₃ -C₆ -cycloalkyl or C₂ -C₆ -alkenyl; R⁷ is hydrogen, C₁ -C₆ -alkyl, C₄-C₈ -cycloalkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl,(C₁ -C₆ -alkyl)carbonyl, (C₃ -C₆ -alkenyl)carbonyl, (C₃ -C₆-alkynyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, (C₂ -C₆ -alkenyloxy)carbonyl, (C₂ -C₆ -alkynyloxy) carbonyl, (C₁ -C₆ -alkylthio) carbonyl,C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylcarbamoyl, where each of the lastmentioned 14 radicals is unsubstituted or carries one to threesubstituents selected from the group consisting ofnitro, cyano, halogen,C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈ cycloalkoxy C₃ -C₆-alkenyloxy C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆-alkylthio, (C₁ -C₆ -alkyl) carbonyl, (C₁ -C₆ -alkyl)carbonyloxy, C₁ -C₆-alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylideneaminoxy, C₁ -C₆-alkylcarbamoyl, phenyl, phenoxy or phenylsulfonyl, where the phenylrings are unsubstituted or carry one to three substituents selected fromthe group consisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy and C₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl orheterocyclyloxy group having one to three hetero atoms, selected fromthe group consisting of two oxygen atoms, two sulfur atoms and 3nitrogen atoms, where the heterocycle is saturated, partially or fullyunsaturated or aromatic, and, where the heterocycle is unsubstituted orcarries one to three substituents selected from the group consisting ofhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyland (C₁ -C₆ -alkyl)carbonyl, a group --CO--Z¹ R⁹, --OCO--Z¹ R⁹ or--N(R⁹)R¹⁰, or R⁷ is C₃ -C₈ -cycloalkylcarbonyl, phenylcarbonyl,phenylsulfonyl or phenylcarbamoyl, where these 4 radicals areunsubstituted or carry one to three substituents selected from the groupconsisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy andC₁ -C₆ -haloalkyl; R⁸ is hydrogen, C₃ -C₈ -cycloalkyl, C₁ -C₆-haloalkyl, C₃ -C₆ -alkenyl or C₃ -C₆ -alkynyl, where each of thelast-mentioned 4 radicals is unsubstituted or carries one to threesubstituents selected from the group consisting ofnitro, cyano, halogen,C₃ -C₈ -cycloalkyl, hydroxyl, C₁ -C₆ -alkoxy, C₃ -C₈ -cycloalkoxy, C₃-C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁-C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylideneaminoxy, phenyl, phenoxy or phenylsulfonyl, where the phenylrings are unsubstituted or carry one to three substituents selected fromthe group consisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy and C₁ -C₆ -haloalkyl, a 3- to 7-membered heterocyclyl orheterocyclyloxy group having one to three hetero atoms, selected fromthe group consisting of two oxygen atoms, two sulfur atoms and 3nitrogen atoms, where the heterocycle is saturated, partially or fullyunsaturated or aromatic, and, where the heterocycle is unsubstituted orcarries one to three substituents selected from the group consisting ofhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkyland (C₁ -C₆ -alkyl) carbonyl, a group --CO--Z² R¹¹, --OCO--Z² R¹¹ or--N(R¹¹)R¹² ; Z¹ is a chemical bond, oxygen, sulfur or --N(R¹⁰)--; Z² isa chemical bond, oxygen, sulfur or --N(R¹²)--; R⁹, R¹¹ independently ofone another are hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₈-cycloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl, phenyl or phenyl-C₁ -C₆-alkyl, where the phenyl and the phenyl ring of the phenylalkyl group isunsubstituted or carries one to three radicals selected from the groupconsisting of nitro, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₁ -C₆ -alkoxy or (C₁ -C₆ -alkyl)carbonyl, or Z¹ and R⁹ and/or Z² andR¹¹ in each case together are a 3- to 7-membered heterocycle bonded vianitrogen and having one to three hetero atoms selected from the groupconsisting of two oxygen atoms, two sulfur atoms and 3 nitrogen atoms,where the heterocycle is saturated, partially or fully unsaturated oraromatic and where the heterocycle is unsubstituted or carries one tothree substituents selected from the group consisting of nitro, cyano,halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl and C₁ -C₆ -alkoxy; R¹⁰, R¹²independently of one another are hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₃-C₈ -cycloalkyl or C₁ -C₆ -alkoxy.